List of USP Standards of NCGC00024427-04 on PharmaCompass.com.

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Chemistry

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Also known as: 16590-41-3, Vivitrol, Revia, N-cyclopropylmethylnoroxymorphone, Vivitrex, Celupan
Molecular Formula
C20H23NO4
Molecular Weight
341.4  g/mol
InChI Key
DQCKKXVULJGBQN-XFWGSAIBSA-N
FDA UNII
5S6W795CQM

Naltrexone
Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.
Naltrexone is an Opioid Antagonist. The mechanism of action of naltrexone is as an Opioid Antagonist.
1 2D Structure

Naltrexone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
2.1.2 InChI
InChI=1S/C20H23NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,15,18,22,24H,1-2,5-10H2/t15-,18+,19+,20-/m1/s1
2.1.3 InChI Key
DQCKKXVULJGBQN-XFWGSAIBSA-N
2.1.4 Canonical SMILES
C1CC1CN2CCC34C5C(=O)CCC3(C2CC6=C4C(=C(C=C6)O)O5)O
2.1.5 Isomeric SMILES
C1CC1CN2CC[C@]34[C@@H]5C(=O)CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O
2.2 Other Identifiers
2.2.1 UNII
5S6W795CQM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Antaxone

2. Celupan

3. En 1639a

4. En-1639a

5. En1639a

6. Nalorex

7. Naltrexone Hydrochloride

8. Nemexin

9. Revia

10. Trexan

2.3.2 Depositor-Supplied Synonyms

1. 16590-41-3

2. Vivitrol

3. Revia

4. N-cyclopropylmethylnoroxymorphone

5. Vivitrex

6. Celupan

7. N-cyclopropylmethyl-14-hydroxydihydromorphinone

8. 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one

9. 17-(cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one

10. 5s6w795cqm

11. Chebi:7465

12. En-1639a Free Base

13. Nemexin

14. Nsc-758439

15. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

16. Um-792

17. En-1639a [as Hydrochloride]

18. Dsstox_cid_26313

19. Dsstox_rid_81532

20. Dsstox_gsid_46313

21. Naltrexonum [inn-latin]

22. (4r,4as,7ar)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

23. Naltrexona [inn-spanish]

24. Naltrexona

25. Naltrexonum

26. (-)-naltrexone

27. Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-, (5.alpha.)-

28. (1s,5r,13r,17s)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one

29. Naltrexone [usan:inn:ban]

30. Naltrexone Base Anhydrous

31. Cas-16590-41-3

32. Ccris 3506

33. Hsdb 6750

34. Einecs 240-649-9

35. Brn 3596648

36. Unii-5s6w795cqm

37. (-)naltrexone

38. Pti-555

39. Ncgc00162274-02

40. Vivitrol (tn)

41. Naltrexone [mi]

42. Naltrexone [inn]

43. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;hydrochloride

44. Naltrexone (usan/inn)

45. Prestwick0_000116

46. Prestwick1_000116

47. Prestwick2_000116

48. Prestwick3_000116

49. Naltrexone [hsdb]

50. Naltrexone [usan]

51. Naltrexone [vandf]

52. Naltrexone [mart.]

53. Naltrexone [usp-rs]

54. Naltrexone [who-dd]

55. Us9107954, Naltrexone

56. Schembl34681

57. Bspbio_000132

58. Bidd:gt0405

59. Chembl19019

60. Spbio_002071

61. Bpbio1_000146

62. Gtpl1639

63. Zinc1773

64. 17-(cyclopropylmethyl)-4,5.alpha.-epoxy-3,14-dihydroxymorphinan-6-one

65. Dtxsid4046313

66. Naltrexone [orange Book]

67. Bdbm60212

68. Cid_5485201

69. Cyclopropylmethyl(dihydroxy)[?]one

70. Hms2089o11

71. Bcp07022

72. Ex-a4863

73. Tox21_112007

74. Bdbm50000787

75. Mfcd00242996

76. Pdsp2_000847

77. Akos015994596

78. Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-alpha-epoxy-3,14-dihydroxy-

79. Tox21_112007_1

80. Cs-0880

81. Db00704

82. Hs-0002

83. Naltrexone Component Of Contrave

84. Nsc 758439

85. Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-, (5alpha)-

86. Smp1_000206

87. Ncgc00024427-03

88. Ncgc00024427-04

89. Ncgc00024427-05

90. Ac-36726

91. Hy-76711

92. C07253

93. D05113

94. Ab00174152-14

95. Ab00174152_17

96. Ar-270/43507956

97. Q409587

98. Brd-k88172511-003-21-1

99. Brd-k88172511-310-03-8

100. 3,14-dihydroxy-17-(cyclopropylmethyl)-4,5alpha-epoxymorphinan-6-one

101. 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxmorphinan-6-one, (5.alpha.)-

102. Naltrexone Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

103. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-bis(oxidanyl)-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;hydrochloride

104. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7ah)-one

105. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one

106. 4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0~1,13~.0~5,17~.0~7,18~]octadeca-7(18),8,10-trien-14-one

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 341.4 g/mol
Molecular Formula C20H23NO4
XLogP31.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass341.16270821 g/mol
Monoisotopic Mass341.16270821 g/mol
Topological Polar Surface Area70 Ų
Heavy Atom Count25
Formal Charge0
Complexity621
Isotope Atom Count0
Defined Atom Stereocenter Count4
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 NameRevia
PubMed HealthNaltrexone
Drug ClassesEthanol Dependency, Opioid Dependency, Toxicology-Antidote Agent
Drug LabelREVIA (naltrexone hydrochloride tablets USP), an opioid antagonist, is a synthetic congener of oxymorphone with no opioid agonist properties. Naltrexone differs in structure from oxymorphone in that the methyl group on the nitrogen atom is replaced...
Active IngredientNaltrexone hydrochloride
Dosage FormTablet
RouteOral
Strength50mg
Market StatusPrescription
CompanyTeva Womens

2 of 4  
Drug NameVivitrol
PubMed HealthNaltrexone
Drug ClassesEthanol Dependency, Opioid Dependency, Toxicology-Antidote Agent
Active IngredientNaltrexone
Dosage FormFor suspension, extended release
RouteIntramuscular
Strength380mg/vial
Market StatusPrescription
CompanyAlkermes

3 of 4  
Drug NameRevia
PubMed HealthNaltrexone
Drug ClassesEthanol Dependency, Opioid Dependency, Toxicology-Antidote Agent
Drug LabelREVIA (naltrexone hydrochloride tablets USP), an opioid antagonist, is a synthetic congener of oxymorphone with no opioid agonist properties. Naltrexone differs in structure from oxymorphone in that the methyl group on the nitrogen atom is replaced...
Active IngredientNaltrexone hydrochloride
Dosage FormTablet
RouteOral
Strength50mg
Market StatusPrescription
CompanyTeva Womens

4 of 4  
Drug NameVivitrol
PubMed HealthNaltrexone
Drug ClassesEthanol Dependency, Opioid Dependency, Toxicology-Antidote Agent
Active IngredientNaltrexone
Dosage FormFor suspension, extended release
RouteIntramuscular
Strength380mg/vial
Market StatusPrescription
CompanyAlkermes

4.2 Therapeutic Uses

Narcotic Antagonists

National Library of Medicine's Medical Subject Headings. Naltrexone. Online file (MeSH, 2017). Available from, as of Oct 4, 2017: https://meshb.nlm.nih.gov/search


/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. Naltrexone is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of August 30, 2017: https://clinicaltrials.gov/


Naltrexone hydrochloride is designated an orphan drug by the US Food and Drug Administration (FDA) and is used orally for its opiate antagonist effects as an adjunct to a medically supervised behavior modification program in the maintenance of opiate cessation (opiate-free state) in individuals formerly physically dependent on opiates and who have successfully undergone detoxification. /Included in US product label/

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2318


Naltrexone is used orally or im in the management of alcohol dependence in conjunction with a comprehensive management program that includes psychosocial support. /Included in US product label/

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2318


For more Therapeutic Uses (Complete) data for Naltrexone (31 total), please visit the HSDB record page.


4.3 Drug Warning

Naltrexone hydrochloride is contraindicated in: 1. Patients receiving opioid analgesics. 2. Patients currently dependent on opioids, including those currently maintained on opiate agonists (e.g., methadone ) or partial agonists (e.g., buprenorphine). 3. Patients in acute opioid withdrawal. 4. Any individual who has failed the naloxone challenge test or who has a positive urine screen for opioids. 5. Any individual with a history of sensitivity to naltrexone hydrochloride or any other components of this product. It is not known if there is any cross-sensitivity with naloxone or the phenanthrene containing opioids.

NIH; DailyMed. Current Medication Information for Naltrexone hydrochloride tablet, film coated (Updated: February 2017). Available from, as of October 12, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=49aa3d6d-2270-4615-aafa-b440859ab870


Cases of hepatitis and clinically significant liver dysfunction were observed in association with naltrexone hydrochloride exposure during the clinical development program and in the postmarketing period. Transient, asymptomatic hepatic transaminase elevations were also observed in the clinical trials and postmarketing period. When patients presented with elevated transaminases, there were often other potential causative or contributory etiologies identified, including pre-existing alcoholic liver disease, hepatitis B and/or C infection, and concomitant usage of other potentially hepatotoxic drugs. Although clinically significant liver dysfunction is not typically recognized as a manifestation of opioid withdrawal, opioid withdrawal that is precipitated abruptly may lead to systemic sequelae, including acute liver injury. Patients should be warned of the risk of hepatic injury and advised to seek medical attention if they experience symptoms of acute hepatitis. Use of naltrexone hydrochloride should be discontinued in the event of symptoms and/or signs of acute hepatitis.

NIH; DailyMed. Current Medication Information for Naltrexone hydrochloride tablet, film coated (Updated: February 2017). Available from, as of October 12, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=49aa3d6d-2270-4615-aafa-b440859ab870


An increase in naltrexone AUC of approximately 5- and 10-fold in patients with compensated and decompensated liver cirrhosis, respectively, compared with subjects with normal liver function has been reported. These data also suggest that alterations in naltrexone bioavailability are related to liver disease severity.

NIH; DailyMed. Current Medication Information for Naltrexone hydrochloride tablet, film coated (Updated: February 2017). Available from, as of October 12, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=49aa3d6d-2270-4615-aafa-b440859ab870


Studies to evaluate possible interactions between naltrexone hydrochloride and drugs other than opiates have not been performed. Consequently, caution is advised if the concomitant administration of naltrexone hydrochloride and other drugs is required. The safety and efficacy of concomitant use of naltrexone hydrochloride and disulfiram is unknown, and the concomitant use of two potentially hepatotoxic medications is not ordinarily recommended unless the probable benefits outweigh the known risks. Lethargy and somnolence have been reported following doses of naltrexone hydrochloride and thioridazine. Patients taking naltrexone hydrochloride may not benefit from opioid containing medicines, such as cough and cold preparations, antidiarrheal preparations, and opioid analgesics. In an emergency situation when opioid analgesia must be administered to a patient receiving naltrexone hydrochloride, the amount of opioid required may be greater than usual, and the resulting respiratory depression may be deeper and more prolonged.

NIH; DailyMed. Current Medication Information for Naltrexone hydrochloride tablet, film coated (Updated: February 2017). Available from, as of October 12, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=49aa3d6d-2270-4615-aafa-b440859ab870


For more Drug Warnings (Complete) data for Naltrexone (36 total), please visit the HSDB record page.


4.4 Drug Indication

Used as an adjunct to a medically supervised behaviour modification program in the maintenance of opiate cessation in individuals who were formerly physically dependent on opiates and who have successfully undergone detoxification. Also used for the management of alcohol dependence in conjunction with a behavioural modification program.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Naltrexone, a pure opioid antagonist, is a synthetic congener of oxymorphone with no opioid agonist properties. Naltrexone is indicated in the treatment of alcohol dependence and for the blockade of the effects of exogenously administered opioids. It markedly attenuates or completely blocks, reversibly, the subjective effects of intravenously administered opioids. When co-administered with morphine, on a chronic basis, naltrexone blocks the physical dependence to morphine, heroin and other opioids. In subjects physically dependent on opioids, naltrexone will precipitate withdrawal symptomatology.


5.2 MeSH Pharmacological Classification

Alcohol Deterrents

Substances interfering with the metabolism of ethyl alcohol, causing unpleasant side effects thought to discourage the drinking of alcoholic beverages. Alcohol deterrents are used in the treatment of alcoholism. (See all compounds classified as Alcohol Deterrents.)


Narcotic Antagonists

Agents inhibiting the effect of narcotics on the central nervous system. (See all compounds classified as Narcotic Antagonists.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
NALTREXONE
5.3.2 FDA UNII
5S6W795CQM
5.3.3 Pharmacological Classes
Mechanisms of Action [MoA] - Opioid Antagonists
5.4 ATC Code

N - Nervous system

N07 - Other nervous system drugs

N07B - Drugs used in addictive disorders

N07BB - Drugs used in alcohol dependence

N07BB04 - Naltrexone


5.5 Absorption, Distribution and Excretion

Absorption

Although well absorbed orally, naltrexone is subject to significant first pass metabolism with oral bioavailability estimates ranging from 5 to 40%.


Route of Elimination

Both parent drug and metabolites are excreted primarily by the kidney (53% to 79% of the dose), however, urinary excretion of unchanged naltrexone accounts for less than 2% of an oral dose and fecal excretion is a minor elimination pathway. The renal clearance for naltrexone ranges from 30 to 127 mL/min and suggests that renal elimination is primarily by glomerular filtration.


Volume of Distribution

1350 L [intravenous administration]


Clearance

~ 3.5 L/min [after IV administration]


Naltrexone hydrochloride is rapidly and almost completely (about 96%) absorbed from the GI tract following oral administration, but the drug undergoes extensive first-pass metabolism in the liver. Only 5-40% of an orally administered dose reaches systemic circulation unchanged. Considerable interindividual variation in absorption of the drug during the first 24 hours after a single dose has been reported. The bioavailability of naltrexone hydrochloride tablets is reportedly similar to that of an oral solution of the drug (not commercially available in the US).

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2325


Peak plasma concentrations of naltrexone and 6-beta-naltrexol (the major metabolite of naltrexone) usually occur within 1 hour following oral administration of the tablets and 0.6 hours following oral administration of the solution. Because orally administered naltrexone undergoes substantial first-pass metabolism, plasma concentrations of 6-beta-naltrexol following oral administration are substantially higher than corresponding concentrations of naltrexone. Following oral administration, the area under the serum concentration-time curve (AUC) for 6-beta-naltrexol is 10-30 times greater than the AUC for naltrexone. Following single- or multiple-dose (i.e., once daily) oral administration of naltrexone hydrochloride 50 mg in healthy individuals, peak plasma concentrations of naltrexone and 6-beta-naltrexol averaged 10.6-13.7 and 109-139 ng/mL, respectively.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2325


Little, if any, accumulation of naltrexone and/or 6-beta-naltrexol appears to occur following chronic administration of the drug. Following chronic administration of naltrexone, plasma concentrations of 6-beta-naltrexol are at least 40% higher than those following administration of a single dose of the drug; however, plasma concentrations of naltrexone and 6-beta-naltrexol 24 hours after each dose of chronically administered drug are similar to concentrations 24 hours after a single dose of the drug in most patients.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2325


Naltrexone hydrochloride is widely distributed throughout the body, but considerable interindividual variation in distribution parameters during the first 24 hours following a single oral dose has been reported. Following subcutaneous administration of radiolabeled drug in rats, the drug distributes into CSF within 30 minutes. In animals, CSF naltrexone concentrations are reported to be approximately 30% of concurrent peak plasma concentrations. The drug and its metabolites have been shown to distribute into saliva and erythrocytes following oral administration in humans.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2325


For more Absorption, Distribution and Excretion (Complete) data for Naltrexone (13 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic. When administered orally, naltrexone undergoes extensive biotransformation and is metabolized to 6 beta-naltrexol (which may contribute to the therapeutic effect) and other minor metabolites.


Naltrexone is metabolized in the liver principally by reduction of the 6-keto group of naltrexone to 6-beta-naltrexol (6-beta-hydroxynaltrexone). Naltrexone also undergoes metabolism by catechol-O-methyl transferase (COMT) to form 2-hydroxy-3-methoxy-6-beta-naltrexol (HMN) and 2-hydroxy-3-methoxynaltrexone. Several minor metabolites have also been identified, including noroxymorphone and 3-methoxy-6-beta-naltrexol. Because oral but not im administration of naltrexone results in substantial first-pass hepatic metabolism of the drug, 6-beta-naltrexol concentrations following im administration are substantially lower than concentrations of the metabolite obtained following oral administration. Naltrexone does not appear to inhibit or induce its own metabolism following chronic administration. Cytochrome P-450 (CYP) isoenzymes are not involved in the metabolism of naltrexone. Naltrexone and its metabolites undergo conjugation with glucuronic acid. The major fraction of total drug and metabolites in both plasma and urine consists of conjugated metabolites. The drug and its metabolites may undergo enterohepatic circulation.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2325


Metabolites of naltrexone may contribute to the opiate antagonist activity of the drug. Like naltrexone, 6-beta-naltrexol is an essentially pure opiate antagonist, with a potency of 6-8% that of naltrexone in precipitating withdrawal symptoms in dogs physically dependent on morphine and 1.25-2% that of naltrexone in mice. Because of its weak affinity for opiate receptors, 2-hydroxy-3-methoxy-6-beta-naltrexol (HMN) may not contribute appreciably to the opiate antagonist activity of naltrexone; however, the in vivo opiate antagonist activity of HMN or 2-hydroxy-3-methoxynaltrexone has not been studied. Noroxymorphone, a minor metabolite of naltrexone, is a potent opiate agonist and may be responsible for the agonist activity (eg, miosis) that occurs infrequently in individuals receiving naltrexone.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2325


Naltrexone and its metabolites (unconjugated and conjugated) are excreted principally in urine via glomerular filtration; 6-beta-naltrexol, conjugated 6-beta-naltrexol, and conjugated naltrexone are also excreted via tubular secretion. Naltrexone may also undergo partial reabsorption by the renal tubules. Following single- or multiple-dose oral administration of naltrexone hydrochloride, respectively, approximately 38-60 or 70% of a dose has been recovered in urine, principally as 6-beta-naltrexol (conjugated and unconjugated). Most urinary excretion of naltrexone occurs within the first 4 hours after oral administration. Less than 2% of an orally administered dose is excreted unchanged in urine within 24 hours. Approximately 5-10, 19-35, 7-16, 3.5-4.6, and 0.45% of an oral dose are excreted in urine as conjugated naltrexone, 6-beta-naltrexol, conjugated 6-beta-naltrexol, 2-hydroxy-3-methoxy-6-beta-naltrexol (HMN), and 2-hydroxy-3-methoxynaltrexone, respectively, within 24 hours. Less than 5% of a dose is excreted in feces, principally as 6-beta-naltrexol, within 24 hours following single- or multiple-dose oral administration of the drug. Following oral administration of 50 mg of radiolabeled naltrexone in one patient, approximately 93% of the radiolabeled dose was excreted within 133 hours; about 79 and 14% were excreted in urine and feces, respectively.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2325-6


Following im administration of naltrexone extended-release injection, the half-life of naltrexone and 6-beta-naltrexol is 5-10 days.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2326


For more Metabolism/Metabolites (Complete) data for Naltrexone (6 total), please visit the HSDB record page.


Naltrexone has known human metabolites that include Naltrexone-3-glucuronide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

4 hours for naltrexone and 13 hours for the active metabolite 6 beta-naltrexol.


Plasma concentrations of naltrexone and 6-beta-naltrexol, the major metabolite, appear to decline in a biphasic manner during the first 24 hours following a single oral dose or during chronic administration of the drug. Following oral administration of single or multiple doses of naltrexone hydrochloride, the plasma half-lives of naltrexone and 6-beta-naltrexol in the initial phase (t1/2 alpha) average 1.1-3.9 and 2.3-3.1 hours, respectively, and the plasma half-lives in the terminal phase (t1/2 beta) average 9.7-10.3 and 11.4-16.8 hours, respectively. Plasma concentrations of naltrexone and 6-beta-naltrexol have also been reported to decline in a triphasic manner following oral administration, with a terminal elimination half-life after the first 24 hours of 96 hours for naltrexone and 18 hours for 6-beta-naltrexol, possibly resulting from initial distribution into body tissues and subsequent redistribution into systemic circulation.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2325


Pharmacokinetics of naltrexone hydrochloride (NTX) and naltrexone glucuronide was studied in the dog using HPLC-electrochemical detection with naloxone as internal standard. After iv 5 mg or po 10 mg NTX, ... the elimination half-lives of NTX were 78 +/- 6 min and 74 +/- 6 min, respectively. ... The major metabolite of NTX in dog plasma was beta-glucuronidase-hydrolyzable conjugate. Dosing NTX intravenously and orally, ... the elimination half-lives of the glucuronide from plasma were 3.4 hr and 12.6 hr, respectively.

PMID:9208648 Li H et al; Yao Xue Xue Bao 31 (4): 254-7 (1996)


5.8 Mechanism of Action

Naltrexone is a pure opiate antagonist and has little or no agonist activity. The mechanism of action of naltrexone in alcoholism is not understood; however, involvement of the endogenous opioid system is suggested by preclinical data. Naltrexone is thought to act as a competitive antagonist at mc, , and receptors in the CNS, with the highest affintiy for the receptor. Naltrexone competitively binds to such receptors and may block the effects of endogenous opioids. This leads to the antagonization of most of the subjective and objective effects of opiates, including respiratory depression, miosis, euphoria, and drug craving. The major metabolite of naltrexone, 6--naltrexol, is also an opiate antagonist and may contribute to the antagonistic activity of the drug.


Naltrexone competes for opiate receptors and displaces opioid drugs from these receptors, thus reversing their effects. It is capable of antagonizing all opiate receptors.

Papich, M.G. Saunders Handbook of Veterinary Drugs Small and Large Animal. 3rd ed. St. Louis, MO: Elsevier Saunders, 2011, p. 533


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11-Jan-2021
31-Aug-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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FDA Orange Book

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01

ALKERMES

Ireland
26th North American ISSX
Not Confirmed
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ALKERMES

Ireland
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26th North American ISSX
Not Confirmed

NALTREXONE

Brand Name : VIVITROL

Dosage Form : FOR SUSPENSION, EXTENDED RELEASE;INTRAMUSCULAR

Dosage Strength : 380MG/VIAL

Approval Date : 2006-04-13

Application Number : 21897

RX/OTC/DISCN : RX

RLD : Yes

TE Code :

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02

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

NALTREXONE

Brand Name : NALTREXONE

Dosage Form : FOR SUSPENSION, EXTENDED RELEASE;INTRAMUSCULAR

Dosage Strength : 380MG/VIAL

Approval Date : 2023-07-06

Application Number : 213195

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

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