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Cephaloridine

Cephaloridine

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Also known as: Cefaloridine, 50-59-9, Cefaloridin, Cephaloridin, Cephaloridinum, Cefalorizin

Molecular Formula

C₁₉H₁₇N₃O₄S₂

Molecular Weight

415.5 g/mol

InChI Key

CZTQZXZIADLWOZ-CRAIPNDOSA-N

FDA UNII

LVZ1VC61HB

A cephalosporin antibiotic.

1 2D Structure

Cephaloridine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C19H17N3O4S2/c23-14(9-13-5-4-8-27-13)20-15-17(24)22-16(19(25)26)12(11-28-18(15)22)10-21-6-2-1-3-7-21/h1-8,15,18H,9-11H2,(H-,20,23,25,26)/t15-,18-/m1/s1

2.1.3 InChI Key

CZTQZXZIADLWOZ-CRAIPNDOSA-N

2.1.4 Canonical SMILES

C1C(=C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CS3)C(=O)[O-])C[N+]4=CC=CC=C4

2.1.5 Isomeric SMILES

C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CS3)C(=O)[O-])C[N+]4=CC=CC=C4

2.2 Other Identifiers

2.2.1 UNII

LVZ1VC61HB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cefaloridine

2. Cephalomycine

3. Cephaloridin

4. Ceporin

2.3.2 Depositor-Supplied Synonyms

1. Cefaloridine

2. 50-59-9

3. Cefaloridin

4. Cephaloridin

5. Cephaloridinum

6. Cefalorizin

7. Cepaloridin

8. Cephalomycine

9. Ceflorin

10. Cepalorin

11. Loridine

12. Cefaloridina

13. Cefaloridinum

14. Kefloridin

15. Ceporin

16. Glaxoridin

17. Chebi:3537

18. N-(7-(2'-thienylacetamidoceph-3-ylmethyl))-pyridinium-2-carboxylate

19. Aliporina

20. N-(7-((2-thienyl)acetamido)ceph-3-em-3-ylmethyl)pyridinium-4-carboxylate

21. Cefaloridine [inn]

22. 7-((2-thienyl)acetamido)-3-(1-pyridylmethyl)cephalosporanic Acid

23. Intrasporin

24. Lvz1vc61hb

25. Ampligram

26. Ceporan

27. Ceporine

28. Cilifor

29. Deflorin

30. Faredina

31. Keflodin

32. Keflordin

33. Kefspor

34. Lloncefal

35. Sefacin

36. Cer

37. Betaine Cephaloridine

38. (6r,7r)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

39. (6r,7r)-8-oxo-3-(pyridinium-1-ylmethyl)-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

40. Cephaloridine (usan)

41. Vioviantine

42. Sasperin

43. Verolgin

44. Sch 11527

45. Cephaloridine [usan]

46. Pyridinium, 1-((2-carboxy-8-oxo-7-((2-thienylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)-oct-2-en-3-yl)methyl)-, Hydroxide, Inner Salt, (6r-trans)-

47. Lilly 40602

48. Ceph 87/4

49. Cefaloridinum [inn-latin]

50. 3-(pyridinium-1-ylmethyl)-7beta-[(2-thienylacetyl)amino]-3,4-didehydrocepham-4-carboxylate

51. Cefaloridina [inn-spanish]

52. (6r,7r)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

53. Hsdb 3023

54. Einecs 200-052-6

55. Unii-lvz1vc61hb

56. Cephaloridine [usan:usp]

57. 7-(thiophene-2-acetamido)-3-(1-pyridylmethyl)-3-cephem-4-carboxylic Acid Betaine

58. (6r,7r)-1-((2-carboxy-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)pyridinium Hydroxide, Inner Salt

59. Kefloridin (tn)

60. Ncgc00094956-01

61. Cefaloridine (jan/inn)

62. Dsstox_cid_2782

63. Cefaloridine [jan]

64. Cephaloridine [mi]

65. Pyridinium, 1-((2-carboxy-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-, Hydroxide, Inner Salt

66. Epitope Id:120366

67. Schembl3936

68. 7-(alpha-(2-thienyl)acetamido)-3-(1-pyridylmethyl)-3-cephem-4-carboxylic Acid Betaine

69. Cephaloridine [hsdb]

70. Dsstox_rid_76727

71. Dsstox_gsid_22782

72. Cefaloridine [mart.]

73. 1-((7'-beta-(2-(2-thienyl)acetamido)-8'-oxo-1'-aza-5'-thiabicyclo(4.2.0)-oct-2'-en-3'-yl)methyl)pyridinium-2'-carboxylate

74. Pyridinium, 1-((2-carboxy-8-oxo-7-((2-thienylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-, Inner Salt, (6r-trans)-

75. Cefaloridine [who-dd]

76. Chembl316157

77. Dtxsid9022782

78. Schembl23270209

79. Gtpl12189

80. Hy-b2072

81. Tox21_111368

82. Bdbm50103624

83. Akos016014429

84. Db09008

85. Cas-50-59-9

86. 7-(.alpha.-(2-thienyl)acetamido)-3-(1-pyridylmethyl)-3-cephem-4-carboxylic Acid Betaine

87. Cs-0017449

88. D01075

89. Q5063323

90. 7-[.alpha.(2-thienyl)-acetoamido]-3-(1-pyridylmethyl)-3-cephem-4-carboxylic Acid Betaine

91. ((6r,7r)-1-((2-carboxy-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)pyridinium Hydroxide, Inner Salt

92. (6r,7r)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)- 7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1- Azabicyclo[4.2.0]oct-2-ene-2-carboxylate

93. (6r,7r)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₇N₃O₄S₂
Molecular Weight	415.5 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	415.06604838 g/mol
Monoisotopic Mass	415.06604838 g/mol
Topological Polar Surface Area	147 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	687
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Cephalosporins

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

GENERAL RANGE OF ACTIVITY & ANTIBACTERIAL SPECTRUM OF CEPHALORIDINE CLOSELY APPROX THAT OF CEPHALOTHIN, ALTHOUGH SOME STRAINS OF E COLI MAY BE SOMEWHAT MORE SENSITIVE TO FORMER. IT ALSO APPEARS TO BE MORE ACTIVE THAN CEPHALOTHIN AGAINST CL PERFRINGENS (WELCHII). MYCOBACTERIUM FORTUITUM IS SENSITIVE TO CEPHALORIDINE...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1160

CEPHALORIDINE...GIVEN PARENTERALLY & SUBCONJUNCTIVALLY TO TREAT INTRAOCULAR INFECTIONS & MAY BE ADMIN TOPICALLY & SUBCONJUNCTIVALLY TO TREAT CORNEAL ULCERS.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 957

CEPHALORIDINE IS EFFECTIVE IN THERAPY OF BRONCHITIS DUE TO H INFLUENZAE, BUT OTHER AGENTS OFTEN PRODUCE BETTER RESULTS, THIS DRUG HAS ALSO BEEN FOUND USEFUL WHEN EMPLOYED AS AEROSOL IN PATIENT WITH PURULENT BRONCHITIS.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1163

For more Therapeutic Uses (Complete) data for CEPHALORIDINE (10 total), please visit the HSDB record page.

4.2 Drug Warning

CEPHALORIDINE ACCUM IN BLOOD OF PATIENTS WITH DECR RENAL FUNCTION, & IN AZOTEMIC PATIENTS PLASMA CONCN ARE VERY HIGH; SINGLE DOSE OF 1 G IM YIELDS DETECTABLE CONCN FOR AS LONG AS 4 DAYS. ...CEPHALORIDINE SHOULD NOT BE GIVEN TO SUCH PATIENTS, SINCE IT IS NEPHROTOXIC.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161

WHILE CEPHALORIDINE PRODUCES LESS IRRITATION /THAN CEPHALOTHIN/, ITS NEPHROTOXICITY OUTWEIGHS THIS ADVANTAGE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1163

IN 48-HR HUMAN INFANTS...CEPHALORIDINE...HAVE VERY LONG PLASMA T/2, & TOXIC CONCN ARE REACHED WHEN DOSES ARE LOWERED CONSIDERABLY.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 681

CEPHALORIDINE IS INJECTED EITHER IM OR IV. ... SINCE OTHER, LESS TOXIC CEPHALOSPORINS ARE AVAIL, THERE IS NO REASON TO RECOMMEND THIS PREPN.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1162

For more Drug Warnings (Complete) data for CEPHALORIDINE (7 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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

5.2 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DB - First-generation cephalosporins

J01DB02 - Cefaloridine

5.3 Absorption, Distribution and Excretion

Route of Elimination

Renal.

.../CEPHALORIDINE/ POORLY ABSORBED FROM GI TRACT. PEAK PLASMA CONCN ARE REACHED ABOUT 30 MIN AFTER DRUG IS INJECTED; 10 TO 20% OF PLASMA CEPHALORIDINE IS BOUND TO PROTEIN.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161

IM INJECTIONS OF 0.5 & 1 G YIELD PEAK PLASMA CONCN OF 15 & 30 UG/ML, RESPECTIVELY. APPROX 75% OF GIVEN DOSE IS EXCRETED IN URINE, MAINLY BY GLOMERULAR FILTRATION. CEPHALORIDINE ACCUM IN BLOOD OF PATIENTS WITH DECR RENAL FUNCTION, & IN AZOTEMIC PATIENTS PLASMA CONCN ARE VERY HIGH...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161

PLACENTAL DRUG TRANSFER- CEPHALORIDINE: TIME TO APPEAR IN FETUS 30 MIN; TIME TO FETAL/MATERNAL CONCN EQUIL 5 HR. /FROM TABLE/

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 101

.../CEPHALORIDINE/ READILY PENETRATE NORMAL EYE FOLLOWING SYSTEMIC OR SUBCONJUNCTIVAL ADMIN...

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 957

...CEPHALORIDINE...SHOWN...TO PENETRATE INTO BONE TO VERY LIMITED EXTENT AFTER SC OR ORAL DOSES TO RATS. RATIOS OF BONE TO SERUM CONCN AVG...1:7 FOR CEPHALORIDINE...DURING 0.25-4 HR AFTER DOSING.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 452

5.4 Biological Half-Life

.../CEPHALORIDINE/ PEAK PLASMA CONCN ARE REACHED ABOUT 30 MIN AFTER DRUG IS INJECTED... WHILE ITS T/2 (60 TO 90 MIN)...ONLY SMALL AMT ARE DETECTABLE AFTER 8 HR.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161

/IN RATS/ RATIOS OF BONE TO SERUM CONCN AVG...1:7 FOR CEPHALORIDINE...DURING 0.25-4 HR AFTER /ORAL OR SC/ DOSING. DESPITE DIFFERENCES IN CONCN, T/2 IN BONE & SERUM WERE SIMILAR.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 452

5.5 Mechanism of Action

CEPHALOTHIN & ITS CONGENERS INHIBIT BACTERIAL CELL-WALL SYNTHESIS IN MANNER SIMILAR TO THAT OF PENICILLIN. /CEPHALOSPORINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1160

Cephaloglycin and cephaloridine are acutely toxic to the proximal renal tubule, in part because of their cellular uptake by a contraluminal anionic secretory carrier and in part through their intracellular attack on the mitochondrial transport and oxidation of tricarboxylic acid (TCA) cycle anionic substrates. Preliminary studies with cephaloglycin have provided evidence of a role of fatty acid (FA) metabolism in its nephrotoxicity, and work with cephaloridine has shown it to be a potent inhibitor of renal tubular cell and mitochondrial carnitine (Carn) transport.

PMID:7887988 Tune BM, Hsu CY; Biochem Pharmacol 49 (5): 727-34 (1995)