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Prestwick3_000158
Also known as: Framycetin, Neomycin b, Fradiomycin, Mycifradin, Soframycin, Fradiomycin b
Molecular Formula
C23H46N6O13
Molecular Weight
614.6  g/mol
InChI Key
PGBHMTALBVVCIT-VCIWKGPPSA-N
FDA UNII
4BOC774388

A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed)
1 2D Structure

Prestwick3_000158

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol
2.1.2 InChI
InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
2.1.3 InChI Key
PGBHMTALBVVCIT-VCIWKGPPSA-N
2.1.4 Canonical SMILES
C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N
2.1.5 Isomeric SMILES
C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)N
2.2 Other Identifiers
2.2.1 UNII
4BOC774388
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Antibiotic 10676

2. Framycetin

3. Framycetin Sulfate

4. Neomycin B

5. Neomycin B Sulfate

6. Soframycin

7. Sulfate, Framycetin

8. Sulfate, Neomycin B

2.3.2 Depositor-Supplied Synonyms

1. Framycetin

2. Neomycin B

3. Fradiomycin

4. Mycifradin

5. Soframycin

6. Fradiomycin B

7. Actiline

8. Enterfram

9. Framygen

10. Actilin

11. Neomas

12. Fradiomycinum

13. Framicetina

14. Framycetine

15. Framycetinum

16. 119-04-0

17. Caswell No. 595

18. Nivemycin

19. Neomycin B Sulfate

20. 1404-04-2

21. Antibiotic 10676

22. Neomycin Sulfate

23. Neomycin Solution

24. Neobrettin

25. Usaf Cb-19

26. Ccris 5462

27. Framidal

28. Framycin

29. Francetin

30. Dekamycin Iii

31. Hsdb 3242

32. Soframycine

33. Framycetin (inn)

34. Neo-rx

35. Antibiotique

36. Myacyne

37. Neolate

38. (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(1r,2r,3s,4r,6s)-4,6-diamino-2-[(2s,3r,4s,5r)-4-[(2r,3r,4r,5s,6s)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol

39. Antibiotique Ef 185

40. Neomycin Sulphate

41. Chebi:7508

42. Vonamycin Powder V

43. (1r,2r,3s,4r,6s)-4,6-diamino-2-{[3-o-(2,6-diamino-2,6-dideoxy-beta-l-idopyranosyl)-beta-d-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2,6-diamino-2,6-dideoxy-alpha-d-glucopyranoside

44. Neomcin

45. Neomin

46. 4boc774388

47. Neomicina [dcit]

48. Framycetinum [inn-latin]

49. Neomicina

50. Neomycine

51. Neomycinum

52. Pimavecort

53. Framycetin [inn]

54. Neomycine [inn-french]

55. Neomycinum [inn-latin]

56. Framycetine [inn-french]

57. Nmy

58. Framicetina [inn-spanish]

59. Framycetin [inn:ban:dcf]

60. Bycomycin

61. Jernadex

62. Neomycin [inn:ban]

63. Einecs 204-292-2

64. Einecs 215-766-3

65. Epa Pesticide Chemical Code 006303

66. Brn 0101621

67. Mycerin

68. Unii-i16qd7x297

69. Unii-4boc774388

70. Antibiotic 956

71. (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(1r,2r,3s,4r,6s)-4,6-diamino-2-[(2s,3r,4s,5r)-4-[(2r,3r,4r,5s,6s)-3-amino-6-(aminomethyl)-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-3-hydroxy-cyclohexoxy]tetrahydropyran-3,4-diol

72. Neomycinb

73. Antibiotic Produced By Streptomyces Decaris. Neomycin B

74. Neomycin B [mi]

75. Prestwick3_000158

76. Kdr Kinase Inhibitor, 3

77. Bdbm19

78. Neomycin B; Fradiomycin B

79. Schembl3279

80. Framycetin [who-dd]

81. Bspbio_000296

82. Gtpl709

83. Neomycin B [usp-rs]

84. 4-18-00-07476 (beilstein Handbook Reference)

85. D-streptamine, O-2,6-diamino-2,6-dideoxy-alpha-d-glucopyranosyl-(1-4)-o-(o-2,6-diamino-2,6-dideoxy-beta-l-idopyranosyl-(1-3)-beta-d-ribofuranosyl-(1-5))-2-deoxy-

86. Bpbio1_000326

87. Chembl184618

88. Dtxsid2023359

89. Hms2089p15

90. I16qd7x297

91. Zinc71928291

92. Akos024284361

93. Cs-6390

94. Db00452

95. Ncgc00179612-01

96. D-streptamine, O-2,6-diamino-2,6-dideoxy-.beta.-l-idopyranosyl-(1.->3)-o-.beta.-d-ribofuranosyl-(1->5)]-o-[2,6-diamino-2,6-dideoxy-.alpha.-d-glucopyranosyl-(1->4)]-2-deoxy

97. Hy-17624

98. Ab00443887

99. C01737

100. D05140

101. Ab00443887-03

102. Mycifradin; Neomas; Pimavecort; Vonamycin

103. Antibiotic Produced By Streptomyces Decaris

104. J-004060

105. Q4492348

106. Brd-k71013094-065-01-2

107. (2r,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-{[(1r,2r,3s,4r,6s)-4,6-diamino-2-{[(2s,3r,4s,5r)-4-{[(2r,3r,4r,5s,6s)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol

108. (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-{[(2r,3s,4r,5s)-5-{[(1r,2r,3s,5r,6s)-3,5-diamino-2-{[(2r,3r,4r,5s,6r)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol

109. 11004-65-2

110. 6-(2-{(4s,2r,3r,5r)-4-[(5s,6s,2r,3r,4r)-3-amino-6-(aminomethyl)-4,5-dihydroxy( 2h-3,4,5,6-tetrahydropyran-2-yloxy)]-3-hydroxy-5-(hydroxymethyl)oxolan-2-yloxy }(3s,6s,1r,2r,4r)-4,6-diamino-3-hydroxycyclohexyloxy)(3s,2r,4r,5r,6r)-5-amino- 2-(aminomethyl)-2h

111. D-streptamine, O-2,6-diamino-2,6-dideoxy-.alpha.-d-glucopyranosyl-(1->4)-o-(o-2,6-diamino-2,6-dideoxy-.beta.-l-idopyranosyl-(1->3)-.beta.-d-ribofuranosyl-(1->5))-2-deoxy-

112. D-streptamine, O-2,6-diamino-2,6-dideoxy-.beta.-l-idopyranosyl-(1->3)-o-.beta.-d-ribofuranosyl-(1->5)-o-(2,6-diamino-2,6-dideoxy-.alpha.-d-glucopyranosyl-(1->4))-2-deoxy-

113. Wurcs=2.0/3,3,2/[a222h-1b_1-4][a2122h-1a_1-5_2*n_6*n][a2121h-1b_1-5_2*n_6*n]/1-2-3/a1n2-b1n1*1oc^rc^ro*2/4c^sc^rcc^s$3/10n/8n/7o_a3-c1

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 614.6 g/mol
Molecular Formula C23H46N6O13
XLogP3-9
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count19
Rotatable Bond Count9
Exact Mass614.31228554 g/mol
Monoisotopic Mass614.31228554 g/mol
Topological Polar Surface Area353 Ų
Heavy Atom Count42
Formal Charge0
Complexity872
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameNeo-fradin
PubMed HealthNeomycin (By mouth)
Drug ClassesAntibiotic
Active IngredientNeomycin sulfate
Dosage FormSolution
RouteOral
Strengtheq 87.5mg base/5ml
Market StatusPrescription
CompanyX Gen Pharms

2 of 4  
Drug NameNeomycin sulfate
Active IngredientNeomycin sulfate
Dosage FormTablet
RouteOral
Strength500mg
Market StatusPrescription
CompanyOman Pharm Products; Teva; X Gen Pharms

3 of 4  
Drug NameNeo-fradin
PubMed HealthNeomycin (By mouth)
Drug ClassesAntibiotic
Active IngredientNeomycin sulfate
Dosage FormSolution
RouteOral
Strengtheq 87.5mg base/5ml
Market StatusPrescription
CompanyX Gen Pharms

4 of 4  
Drug NameNeomycin sulfate
Active IngredientNeomycin sulfate
Dosage FormTablet
RouteOral
Strength500mg
Market StatusPrescription
CompanyOman Pharm Products; Teva; X Gen Pharms

4.2 Therapeutic Uses

Anti-Bacterial Agents; Protein Synthesis Inhibitors

National Library of Medicine's Medical Subject Headings. Neomycin. Online file (MeSH, 2016). Available from, as of December 5, 2016: https://www.nlm.nih.gov/mesh/2016/mesh_browser/MBrowser.html


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Neomycin is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of February 1, 2017: https://clinicaltrials.gov/ct2/results?term=NEOMYCIN&Search=Search


Neomycin sulfate tablets are indicated as adjunctive therapy as part of a regimen for the suppression of the normal bacterial flora of the bowel, e.g., preoperative preparation of the bowel. It is given concomitantly with erythromycin enteric-coated base. /Included in US product label/

NIH; DailyMed. Current Medication Information for Neomycin Sulfate (Neomycin Sulfate Tablet) (Updated: June 2016). Available from, as of February 16, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3114c827-1923-437a-bc8a-a1ac20327a28


Neomycin sulfate has been shown to be effective adjunctive therapy in hepatic coma by reduction of the ammonia-forming bacteria in the intestinal tract. The subsequent reduction in blood ammonia has resulted in neurologic improvement. /Included in US product label/

NIH; DailyMed. Current Medication Information for Neomycin Sulfate (Neomycin Sulfate Tablet) (Updated: June 2016). Available from, as of February 16, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3114c827-1923-437a-bc8a-a1ac20327a28


For more Therapeutic Uses (Complete) data for Neomycin (14 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ WARNINGS SYSTEMIC ABSORPTION OF NEOMYCIN OCCURS FOLLOWING ORAL ADMINISTRATION AND TOXIC REACTIONS MAY OCCUR. Patients treated with neomycin should be under close clinical observation because of the potential toxicity associated with their use. NEUROTOXICITY (INCLUDING OTOTOXICITY) AND NEPHROTOXICITY FOLLOWING THE ORAL USE OF NEOMYCIN SULFATE HAVE BEEN REPORTED, EVEN WHEN USED IN RECOMMENDED DOSES. THE POTENTIAL FOR NEPHROTOXICITY, PERMANENT BILATERAL AUDITORY OTOTOXICITY AND SOMETIMES VESTIBULAR TOXICITY IS PRESENT IN PATIENTS WITH NORMAL RENAL FUNCTION WHEN TREATED WITH HIGHER DOSES OF NEOMYCIN AND/OR FOR LONGER PERIODS THAN RECOMMENDED. Serial, vestibular and audiometric tests, as well as tests of renal function, should be performed (especially in high-risk patients). THE RISK OF NEPHROTOXICITY AND OTOTOXICITY IS GREATER IN PATIENTS WITH IMPAIRED RENAL FUNCTION. Ototoxicity is often delayed in onset and patients developing cochlear damage will not have symptoms during therapy to warn them of developing eighth nerve destruction and total or partial deafness may occur long after neomycin has been discontinued. Neuromuscular blockage and respiratory paralysis have been reported following the oral use of neomycin. The possibility of the occurrence of neuromuscular blockage and respiratory paralysis should be considered if neomycin is administered, especially to patients receiving anesthetics, neuromuscular blocking agents such as tubocurarine, succinylcholine, decamethonium, or in patients receiving massive transfusions of citrate anticoagulated blood. If blockage occurs, calcium salts may reverse these phenomena but mechanical respiratory assistance may be necessary. Concurrent and/or sequential systemic, oral or topical use of other aminoglycosides, including paromomycin and other potentially nephrotoxic and/or neurotoxic drugs such as bacitracin, cisplatin, vancomycin, amphotericin B, polymyxin B, colistin and viomycin, should be avoided because the toxicity may be additive. Other factors which increase the risk of toxicity are advanced age and dehydration. The concurrent use of neomycin with potent diuretics such as ethacrynic acid or furosemide should be avoided, since certain diuretics by themselves may cause ototoxicity. In addition, when administered intravenously, diuretics may enhance neomycin toxicity by altering the antibiotic concentration in serum and tissue.

NIH; DailyMed. Current Medication Information for Neomycin Sulfate (Neomycin Sulfate Tablet) (Updated: June 2016). Available from, as of February 16, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3114c827-1923-437a-bc8a-a1ac20327a28


VET: Ototoxicity, neuromuscular blockade, and nephrotoxicity are reported most frequently; these effects may vary with the aminoglycoside and dose or interval used, but all members of the group are potentially toxic. Nephrotoxicity is of major concern and may result in renal failure due to acute tubular necrosis with secondary interstitial damage. Aminoglycosides accumulate in proximal tubular epithelial cells, where they are sequestered in lysosomes and interact with ribosomes, mitochondria, and other intracellular constituents to cause cell injury. The greater the ionization (eg, the more the amine groups and the lower the pH), the greater the active uptake. Kidneys must have a drug-free period to eliminate accumulated drugs. As such, persistence of aminoglycosides in plasma and thus urine is likely to predispose the tubular cells to toxicity, and the risk may by reduced by allowing plasma drug concentrations to drop below recommended concentrations (generally 1-2 ug/mL) before the next dose. Nonoliguric renal failure is the usual observation; it is generally reversible if damage is not sufficiently extensive to harm the basement membrane, although recovery may be prolonged. /Aminoglycosides/

Kahn, C.M (ed.).; The Merck Veterinary Manual 10th Edition. Merck & Co. Whitehouse Station NJ. 2010, p. 2277-8


VET: Renal function should be monitored during therapy; however, no indicator of renal disease is sufficiently sensitive to prevent continued damage once nephrotoxicity is detected. Polyuria, decreased urine osmolality, enzymuria, proteinuria, cylindruria, and increased fractional sodium excretion are indicative of aminoglycoside nephrotoxicity. Later, BUN and creatinine concentrations may be increased. Early changes or evidence of nephrotoxicity can be detected in 3-5 days, with more overt signs in 7-10 days. Several factors predispose to aminoglycoside nephrotoxicosis, including age (with young (especially the newborn foal) and old animals being sensitive), compromised renal function, total dose, duration of treatment, dehydration and hypovolemia, aciduria, acidosis, hypomagnesemia, severe sepsis or endotoxemia, concurrent administration of furosemide, and exposure to other potential nephrotoxins (eg, methoxyflurane, amphotericin B, cisplatinum, and perhaps some cephalosporins). In renal insufficiency, generally the interval between doses is prolonged (rather than reducing the dose) to minimize toxicity, while avoiding a negative impact on efficacy. Dosing in the morning may decrease toxicity in diurnal animals. The risk of toxicity is less in alkaline urine. Nephroactive drugs, including those that alter renal vascular response (eg, autoregulation) should be avoided or used cautiously (eg, NSAIDs, diuretics). Treatment with N-acetylcysteine should be considered. /Aminoglycosides/

Kahn, C.M (ed.).; The Merck Veterinary Manual 10th Edition. Merck & Co. Whitehouse Station NJ. 2010, p. 2278


VET: Aminoglycosides can cause ototoxicity, which may manifest as either auditory or vestibular dysfunction. Binding or damage to mitochondria plays a prominent role in ototoxicity. Vestibular injury leads to nystagmus, incoordination, and loss of the righting reflex. The lesion is often irreversible, although physiologic adaptation can occur. Ototoxicity is not unusual in people, but relevance to veterinary patients is not clear. Cats are particularly sensitive to the toxic vestibular effects, although occurrence at therapeutic concentrations after systemic administration is unlikely. However, aminoglycosides should not be administered topically into the ear unless the tympanic membrane is intact. Hearing impairment reflects permanent damage and loss of the hair cells in the organ of Corti. Loss of high-frequency hearing is followed by deafness, which may not be complete if sufficiently low doses or durations were used. Aminoglycosides should be avoided in working dogs that depend on hearing (eg, guide dogs). Factors increasing the risk of vestibular and cochlear damage are the same as for nephrotoxicity but also include preexisting acoustic or vestibular impairment and concurrent treatment with potentially ototoxic drugs. The ototoxic potential is greatest for gentamicin, sisomicin, and neomycin, and least for netilmicin. In people, treatment with N-acetylcysteine has deceased the risk of aminoglycoside ototoxicity. /Aminoglycosides/

Kahn, C.M (ed.).; The Merck Veterinary Manual 10th Edition. Merck & Co. Whitehouse Station NJ. 2010, p. 2278


For more Drug Warnings (Complete) data for Neomycin (39 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of bacterial blepharitis, bacterial bonjunctivitis, corneal injuries, corneal ulcers and meibomianitis. For the prophylaxis of ocular infections following foreign body removal


Oral neomycin sulfate is indicated as an adjunctive therapy in hepatic coma (portal-system encephalopathy) by reducing ammonia-forming bacteria in the intestinal tract. It is strongly recommended that oral neomycin is only used in infections that are proven or strongly suspected to be caused by susceptible bacteria to reduce the risk of the development of drug-resistant bacteria. Neomycin, in combination with polymyxin B sulfates and hydrocortisone in otic suspensions, is used in the treatment of superficial bacterial infections of the external auditory canal caused by organisms susceptible to the antibiotics. This otic formulation is also used in the treatment of infections of mastoidectomy and fenestration cavities caused by organisms susceptible to the antibiotics. The ophthalmic solution containing neomycin in combination with polymyxin B sulfates and dexamethasone is used to treat steroid-responsive inflammatory ocular conditions for which a corticosteroid is indicated and where bacterial infection or a risk of bacterial infection exists.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Framycetin is used for the treatment of bacterial eye infections such as conjunctivitis. Framycetin is an antibiotic. It is not active against fungi, viruses and most kinds of anaerobic bacteria. Framycetin works by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Framycetin is useful primarily in infections involving aerobic bacteria bacteria.


Neomycin mediates its bactericidal action by inhibiting bacterial protein synthesis, thereby suppressing the growth and survival of susceptible bacteria. Following oral administration, the duration of bactericidal activity of neomycin ranged from 48 to 72 hours. By decreasing colonic bacteria that produce ammonia, neomycin was shown to be effective as an adjunctive therapy in hepatic coma to improve neurologic symptoms. Neomycin is active against both gram positive and gram negative organisms, including the major _E. coli_ species resident in the colon as well as the enteropathogenic forms of _E. coli_. It is also active against _Klebsiella_-_Enterobacter_ group. Resistant strains of _E. coli_, _Klebsiella_ and _Proteus spp_. may emerge from neomycin therapy. Neomycin has no antifungal activity and has some activity against some protozoa.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Aminoglycosides [CS]; Aminoglycoside Antibacterial [EPC]
5.4 ATC Code

R01AX08

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AB - Antiinfectives and antiseptics for local oral treatment

A01AB08 - Neomycin


A - Alimentary tract and metabolism

A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

A07A - Intestinal antiinfectives

A07AA - Antibiotics

A07AA01 - Neomycin


B - Blood and blood forming organs

B05 - Blood substitutes and perfusion solutions

B05C - Irrigating solutions

B05CA - Antiinfectives

B05CA09 - Neomycin


D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06A - Antibiotics for topical use

D06AX - Other antibiotics for topical use

D06AX04 - Neomycin


D - Dermatologicals

D09 - Medicated dressings

D09A - Medicated dressings

D09AA - Medicated dressings with antiinfectives

D09AA01 - Framycetin


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01G - Aminoglycoside antibacterials

J01GB - Other aminoglycosides

J01GB05 - Neomycin


R - Respiratory system

R01 - Nasal preparations

R01A - Decongestants and other nasal preparations for topical use

R01AX - Other nasal preparations

R01AX08 - Framycetin


R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AB - Antibiotics

R02AB01 - Neomycin


S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AA - Antibiotics

S01AA03 - Neomycin


S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AA - Antibiotics

S01AA07 - Framycetin


S - Sensory organs

S02 - Otologicals

S02A - Antiinfectives

S02AA - Antiinfectives

S02AA07 - Neomycin


S - Sensory organs

S03 - Ophthalmological and otological preparations

S03A - Antiinfectives

S03AA - Antiinfectives

S03AA01 - Neomycin


5.5 Absorption, Distribution and Excretion

Absorption

Neomycin is poorly absorbed from the gastrointestinal tract. Gastrointestinal absorption of the drug may be increased if inflammatory or ulcerative gastrointestinal disease is present.


Route of Elimination

The small absorbed fraction of neomycin is excreted by the kidney. The unabsorbed portion of the drug is excreted unchanged in the feces.


Volume of Distribution

The small fraction of absorbed neomycin is rapidly distributed in the tissues. The amount of systemically absorbed neomycin is reported to increase cumulatively with each repeated dose administered until a steady state is reached.


Clearance

There is limited information on the clearance rate of neomycin.


Neomycin sulfate is poorly absorbed from the normal gastrointestinal tract. The small absorbed fraction is rapidly distributed in the tissues and is excreted by the kidney in keeping with the degree of kidney function. The unabsorbed portion of the drug (approximately 97%) is eliminated unchanged in the feces.

NIH; DailyMed. Current Medication Information for Neomycin Sulfate (Neomycin Sulfate Tablet) (Updated: June 2016). Available from, as of February 16, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3114c827-1923-437a-bc8a-a1ac20327a28


As with other aminoglycosides, the amount of systemically absorbed neomycin transferred to the tissues increases cumulatively with each repeated dose administered until a steady state is achieved. The kidney functions as the primary excretory path as well as the tissue binding site, with the highest concentration found in the renal cortex. With repeated dosings, progressive accumulation also occurs in the inner ear. Release of tissue-bound neomycin occurs slowly over a period of several weeks after dosing has been discontinued.

NIH; DailyMed. Current Medication Information for Neomycin Sulfate (Neomycin Sulfate Tablet) (Updated: June 2016). Available from, as of February 16, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3114c827-1923-437a-bc8a-a1ac20327a28


In one study in adults with normal renal function, a single 4-g oral dose of neomycin sulfate produced peak plasma neomycin concentrations of 2.5-6.1 ug/mL 1-4 hours after the dose in most patients; low plasma concentrations of the drug were detectable at 8 hours but the drug was undetectable at 24 hours.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016


In adults who received 1-g doses of oral neomycin sulfate and 1-g doses of oral erythromycin at 19, 18, and 9 hours before colorectal surgery, mean peak serum concentrations of neomycin were 0.59 ug/mL and were attained 12 hours after the first dose (i.e., 2 hours after the third dose).

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016


For more Absorption, Distribution and Excretion (Complete) data for Neomycin (16 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

There is limited information on the metabolism of neomycin, as there is limited systemic absorption following drug administration. Metabolism is deemed to be negligible.


Aminoglycosides are not metabolized and are excreted unchanged in the urine primarily by glomerular filtration. /Aminoglycosides/

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 31


5.7 Biological Half-Life

There is limited information on the half-life of neomycin.


The plasma elimination half-life of neomycin usually is 2-3 hours in adults with normal renal function and has been reported to be 12-24 hours in adults with severe renal impairment.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016


5.8 Mechanism of Action

Framycetin binds to specific 30S-subunit proteins and 16S rRNA, four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.


Like other aminoglycoside antibiotic drugs, neomycin inhibits bacterial ribosomes by binding to the 30S ribosomal subunit of susceptible bacteria and disrupting the translational machinery of bacterial protein synthesis. Bacterial translation is normally initiated by the mRNA binding to the 30S ribosomal subunit and subsequent binding with 50S subunit for elongation.


Aminoglycosides are usually bactericidal in action. Although the exact mechanism of action has not been fully elucidated, the drugs appear to inhibit protein synthesis in susceptible bacteria by irreversibly binding to 30S ribosomal subunits. /Aminoglycosides/

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 29


A class of angiogenesis inhibitor has emerged from our mechanistic study of the action of angiogenin, a potent angiogenic factor. Neomycin, an aminoglycoside antibiotic, inhibits nuclear translocation of human angiogenin in human endothelial cells, an essential step for angiogenin-induced angiogenesis. The phospholipase C-inhibiting activity of neomycin appears to be involved, because U-73122, another phospholipase C inhibitor, has a similar effect. In contrast, genistein, oxophenylarsine, and staurosporine, inhibitors of tyrosine kinase, phosphotyrosine phosphatase, and protein kinase C, respectively, do not inhibit nuclear translocation of angiogenin. Neomycin inhibits angiogenin-induced proliferation of human endothelial cells in a dose-dependent manner. At 50 microM, neomycin abolishes angiogenin-induced proliferation but does not affect the basal level of proliferation and cell viability. Other aminoglycoside antibiotics, including gentamicin, streptomycin, kanamycin, amikacin, and paromomycin, have no effect on angiogenin-induced cell proliferation. Most importantly, neomycin completely inhibits angiogenin-induced angiogenesis in the chicken chorioallantoic membrane at a dose as low as 20 ng per egg. These results suggest that neomycin and its analogs are a class of agents that may be developed for anti-angiogenin therapy.

Hu G; Proc Natl Acad Sci U S A 95(17): p.9791-9795 (1998)


... Aminoglycosides are aminocyclitols that kill bacteria by inhibiting protein synthesis as they bind to the 16S rRNA and by disrupting the integrity of bacterial cell membrane. Aminoglycoside resistance mechanisms include: (a) the deactivation of aminoglycosides by N-acetylation, adenylylation or O-phosphorylation, (b) the reduction of the intracellular concentration of aminoglycosides by changes in outer membrane permeability, decreased inner membrane transport, active efflux, and drug trapping, (c) the alteration of the 30S ribosomal subunit target by mutation, and (d) methylation of the aminoglycoside binding site. ... /Aminoglycosides/

PMID:17657587 Shakil S et al; J Biomed Sci 15 (1): 5-14 (2008)


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