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Butorphanol

Butorphanol

Synopsis, Chemistry

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Also known as: Butorphanol tartrate, 58786-99-5, Butorphanol (+)-tartrate salt, Stadol (tn), Butorphanol tartrate salt, Butorphanol tartrate (jan/usp)

Molecular Formula

C₂₅H₃₅NO₈

Molecular Weight

477.5 g/mol

InChI Key

GMTYREVWZXJPLF-BTVKVFNOSA-N

A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain.

1 2D Structure

Butorphanol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol;(2R,3R)-2,3-dihydroxybutanedioic acid

2.1.2 InChI

InChI=1S/C21H29NO2.C4H6O6/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15;5-1(3(7)8)2(6)4(9)10/h6-7,13,15,19,23-24H,1-5,8-12,14H2;1-2,5-6H,(H,7,8)(H,9,10)/t19-,20+,21-;1-,2-/m11/s1

2.1.3 InChI Key

GMTYREVWZXJPLF-BTVKVFNOSA-N

2.1.4 Canonical SMILES

C1CCC2(C3CC4=C(C2(C1)CCN3CC5CCC5)C=C(C=C4)O)O.C(C(C(=O)O)O)(C(=O)O)O

2.1.5 Isomeric SMILES

C1CC[C@]2([C@H]3CC4=C([C@]2(C1)CCN3CC5CCC5)C=C(C=C4)O)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 17-(cyclobutylmethyl)morphinan-3,14-diol

2. Apo-butorphanol

3. Bc 2627

4. Bc-2627

5. Bc2627

6. Beforal

7. Butorphanol

8. Butorphanol Tartrate

9. Dolorex

10. Moradol

11. Stadol

12. Stadol Ns

13. Torbugesic

2.2.2 Depositor-Supplied Synonyms

1. Butorphanol Tartrate

2. 58786-99-5

3. Butorphanol (+)-tartrate Salt

4. Stadol (tn)

5. Butorphanol Tartrate Salt

6. Butorphanol Tartrate (jan/usp)

7. Akos015994595

8. Hs-0001

9. Butorphanol (+)-tartrate Salt, >=99%

10. D00837

11. 786b995

12. Butorphanol Tartrate, United States Pharmacopeia (usp) Reference Standard

2.2.3 Other Synonyms

1. Butorfanol

2. Torate

3. Torbutrol

2.3 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₃₅NO₈
Molecular Weight	477.5 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Exact Mass	477.23626707 g/mol
Monoisotopic Mass	477.23626707 g/mol
Topological Polar Surface Area	159 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	626
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Butorphanol tartrate
Drug Label	Butorphanol tartrate is a synthetically derived opioid agonist-antagonist analgesic of the phenanthrene series. The chemical name is (-)-17-(cyclobutylmethyl) morphinan-3, 14-diol [S-(R,R)] 2,3 dihydroxybutanedioate (1:1) (salt). The molecul...
Active Ingredient	Butorphanol tartrate
Dosage Form	Injectable; Spray, metered
Route	Nasal; Injection
Strength	2mg/ml; 1mg/ml; 1mg/spray
Market Status	Prescription
Company	Bedford; Hikma Farmaceutica; Novex; Mylan; Roxane

2 of 2
Drug Name	Butorphanol tartrate
Drug Label	Butorphanol tartrate is a synthetically derived opioid agonist-antagonist analgesic of the phenanthrene series. The chemical name is (-)-17-(cyclobutylmethyl) morphinan-3, 14-diol [S-(R,R)] 2,3 dihydroxybutanedioate (1:1) (salt). The molecul...
Active Ingredient	Butorphanol tartrate
Dosage Form	Injectable; Spray, metered
Route	Nasal; Injection
Strength	2mg/ml; 1mg/ml; 1mg/spray
Market Status	Prescription
Company	Bedford; Hikma Farmaceutica; Novex; Mylan; Roxane

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antitussive Agents

Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)

Narcotics

Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS. (See all compounds classified as Narcotics.)

Analgesics, Opioid

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)

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 Agonist/Antagonist [EPC]; Partial Opioid Agonists [MoA]; Competitive Opioid Antagonists [MoA]