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Chemistry

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Also known as: Naltrexone hcl, 16676-29-2, Trexan, Depade, Antaxone, Revia
Molecular Formula
C20H24ClNO4
Molecular Weight
377.9  g/mol
InChI Key
RHBRMCOKKKZVRY-ITLPAZOVSA-N
FDA UNII
Z6375YW9SF

Naltrexone Hydrochloride
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.
1 2D Structure

Naltrexone Hydrochloride

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;hydrochloride
2.1.2 InChI
InChI=1S/C20H23NO4.ClH/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;1H/t15-,18+,19+,20-;/m1./s1
2.1.3 InChI Key
RHBRMCOKKKZVRY-ITLPAZOVSA-N
2.1.4 Canonical SMILES
C1CC1CN2CCC34C5C(=O)CCC3(C2CC6=C4C(=C(C=C6)O)O5)O.Cl
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.Cl
2.2 Other Identifiers
2.2.1 UNII
Z6375YW9SF
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Antaxone

2. Celupan

3. En 1639a

4. En-1639a

5. En1639a

6. Nalorex

7. Naltrexone

8. Nemexin

9. Revia

10. Trexan

2.3.2 Depositor-Supplied Synonyms

1. Naltrexone Hcl

2. 16676-29-2

3. Trexan

4. Depade

5. Antaxone

6. Revia

7. Naltrexone (hydrochloride)

8. En-1639a

9. Nih 8503

10. Celupan

11. Nemexin

12. N-cyclopropylmethyl-noroxymorphone Hydrochloride

13. Mls000069607

14. Naltrexone Hydrochloride [usp]

15. Z6375yw9sf

16. Vivitrex

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

18. Nalorex

19. Smr000058767

20. En-1639a (as Hydrochloride)

21. En 1639a

22. (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;hydrochloride

23. Naltrexone Hydrochloride (usp)

24. (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 Hydrochloride

25. Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-, Hydrochloride (1:1), (5alpha)-

26. Ccris 1168

27. Einecs 240-723-0

28. Unii-z6375yw9sf

29. Naltrel

30. Naltrexone.hcl

31. Naltrexone Depot

32. Prestwick_348

33. Mfcd00069324

34. (5alpha)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

35. Revia (tn)

36. Xr-ntx

37. (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

38. Opera_id_1828

39. Naltrexone Monohydrochloride

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

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

42. Schembl37713

43. Mls001076516

44. Mls002153483

45. Mls002695940

46. Cyto-205

47. Chembl1201149

48. Dtxsid50937236

49. Pti-901

50. Chebi:134687

51. Bcp08343

52. Naltrexone Hydrochloride [mi]

53. S2103

54. Vp-004

55. Akos015994597

56. Ccg-268383

57. Cs-0763

58. Hs-0003

59. Nc00693

60. 17-cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

61. Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-alpha-oxy-3,14-dihydoxy-, Hydrochloride

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

63. Naltrexone Hydrochloride [mart.]

64. Naltrexone Hydrochloride [vandf]

65. Naltrexone Hydrochloride [who-dd]

66. Bn164635

67. Hy-76710

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

69. N1176

70. Naltrexone Hydrochloride [green Book]

71. Sw196619-3

72. Naltrexone Hydrochloride [orange Book]

73. D02095

74. Embeda Component Naltrexone Hydrochloride

75. H10489

76. Naltrexone Hydrochloride [ep Monograph]

77. Naltrexone Hydrochloride [usp Monograph]

78. Troxyca Component Naltrexone Hydrochloride

79. 676n292

80. Contrave Component Naltrexone Hydrochloride

81. Naltrexone Hydrochloride Component Of Embeda

82. Naltrexone Hydrochloride Component Of Troxyca

83. Naltrexone Hydrochloride Component Of Contrave

84. Q27096434

85. Z1558290144

86. Naltrexone Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

87. Naltrexone Hydrochloride, European Pharmacopoeia (ep) Reference Standard

88. (5a)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-morphinan-6-one Hydrochloride

89. 17-(cyclopropylmethyl)-3,14-dihydroxy-4,5alpha-epoxymorphinan-6-one Hydrochloride

90. 17-cyclopropylmethyl)-4,5.alpha.-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

91. (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 Hydrochloride

92. (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;hydron;chloride

93. (5alpha,17r)-17-(cyclopropylmethyl)-3,14-dihydroxy-6-oxo-4,5-epoxymorphinan-17-ium Chloride

94. Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-, (5.alpha.)-, Hydrochloride (1:1)

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 377.9 g/mol
Molecular Formula C20H24ClNO4
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass377.1393859 g/mol
Monoisotopic Mass377.1393859 g/mol
Topological Polar Surface Area70 Ų
Heavy Atom Count26
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 Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameNaltrexone hydrochloride
PubMed HealthNaltrexone
Drug ClassesEthanol Dependency, Opioid Dependency, Toxicology-Antidote Agent
Drug LabelNaltrexone hydrochloride, 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 by a cyclopropylmethy...
Active IngredientNaltrexone hydrochloride
Dosage FormTablet
RouteOral
Strength25mg; 100mg; 50mg
Market StatusPrescription
CompanyAccord Hlthcare; Mallinckrodt; Sun Pharma Global; Elite Labs; Barr

2 of 6  
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

3 of 6  
Drug NameVivitrol
Active IngredientNaltrexone
Dosage FormFor suspension, extended release
RouteIntramuscular
Strength380mg/vial
Market StatusPrescription
CompanyAlkermes

4 of 6  
Drug NameNaltrexone hydrochloride
PubMed HealthNaltrexone
Drug ClassesEthanol Dependency, Opioid Dependency, Toxicology-Antidote Agent
Drug LabelNaltrexone hydrochloride, 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 by a cyclopropylmethy...
Active IngredientNaltrexone hydrochloride
Dosage FormTablet
RouteOral
Strength25mg; 100mg; 50mg
Market StatusPrescription
CompanyAccord Hlthcare; Mallinckrodt; Sun Pharma Global; Elite Labs; Barr

5 of 6  
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

6 of 6  
Drug NameVivitrol
Active IngredientNaltrexone
Dosage FormFor suspension, extended release
RouteIntramuscular
Strength380mg/vial
Market StatusPrescription
CompanyAlkermes

5 Pharmacology and Biochemistry
5.1 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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Opioid Antagonists [MoA]; Opioid Antagonist [EPC]

API Reference Price

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19-Jan-2021
26-Oct-2024
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INTERMEDIATES SUPPLIERS

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01

BMWS24
Not Confirmed
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  • fda
  • EDQM
  • WHO-GMP

Virtual BoothFaran Shimi: Leading producer of high-quality APIs & alkaloid opiates, serving major pharmaceutical companies across the Middle East.

CAS Number : 7051-34-5

End Use API : Naltrexone Hydrochloride

About The Company : Faran Shimi Pharmaceutical Company, established in 2001 and affiliated with Golrang Pharmaceutical Investment Co, manufactures high-quality Active Pharmaceutica...

Faran Shimi Pharmaceutical

02

Minakem

France
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothMinakem delivers API, HPAPI, steroids & CDMO services for generics with FDA/GMP certification, regulatory know-how & proven success.

CAS Number : 7051-34-5

End Use API : Naltrexone Hydrochloride

About The Company : MINAKEM is a cGMP custom manufacturer of small molecule API, HPAPI and steroids. All development and manufacturing activities are supported by highly skilled R&...

Minakem Comapny Banner

03

M2i Group

France
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothM2i Group, an integrated CDMO, is your French partner for development & manufacturing in fine chemistry.

CAS Number : 7051-34-5

End Use API : Naltrexone Hydrochloride

About The Company : Integrated solutions for all your projects.
M2i Group provides integrated solutions for all your projects. We offer our clients an integrated partner, fr...

m2i group
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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 90MG...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 90MG;8MG

USFDA APPLICATION NUMBER - 200063

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 100...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 100MG;4MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22321

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 20M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 20MG;0.8MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22321

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 30M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 30MG;1.2MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22321

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 50M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 50MG;2MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22321

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 60M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 60MG;2.4MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22321

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 80M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 80MG;3.2MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22321

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