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Chemistry

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Also known as: (4r,4ar,7ar,12bs)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;2,3-dihydroxybutanedioic acid, .codon, Schembl154972, Chembl2062267
Molecular Formula
C22H27NO9
Molecular Weight
449.4  g/mol
InChI Key
OJHZNMVJJKMFGX-RNWHKREASA-N

Hydrocodone Bitartrate
Narcotic analgesic related to CODEINE, but more potent and more addicting by weight. It is used also as cough suppressant.
1 2D Structure

Hydrocodone Bitartrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;2,3-dihydroxybutanedioic acid
2.1.2 InChI
InChI=1S/C18H21NO3.C4H6O6/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19;5-1(3(7)8)2(6)4(9)10/h3,6,11-12,17H,4-5,7-9H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t11-,12+,17-,18-;/m0./s1
2.1.3 InChI Key
OJHZNMVJJKMFGX-RNWHKREASA-N
2.1.4 Canonical SMILES
CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(=O)CC4.C(C(C(=O)O)O)(C(=O)O)O
2.1.5 Isomeric SMILES
CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3C(=O)CC4.C(C(C(=O)O)O)(C(=O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Codinovo

2. Dicodid

3. Dihydrocodeinone

4. Hycodan

5. Hycon

6. Hydrocodeinonebitartrate

7. Hydrocodon

8. Hydrocodone

9. Hydrocodone Tartrate (1:1), Hydrate (2:5)

10. Hydrocon

11. Robidone

2.2.2 Depositor-Supplied Synonyms

1. (4r,4ar,7ar,12bs)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;2,3-dihydroxybutanedioic Acid

2. .codon

3. Schembl154972

4. Chembl2062267

2.2.3 Other Synonyms

1. Hydrocone

2. Multacodin

3. Hydrocodone

2.3 Create Date
2007-12-05
3 Chemical and Physical Properties
Molecular Weight 449.4 g/mol
Molecular Formula C22H27NO9
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass449.16858144 g/mol
Monoisotopic Mass449.16858144 g/mol
Topological Polar Surface Area154 Ų
Heavy Atom Count32
Formal Charge0
Complexity642
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

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.)


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.)


4.2 FDA Pharmacological Classification
4.2.1 Pharmacological Classes
Opioid Agonists [MoA]; Opioid Agonist [EPC]

DRUG PRODUCT COMPOSITIONS

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 10M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 10MG

USFDA APPLICATION NUMBER - 202880

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 15M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 15MG

USFDA APPLICATION NUMBER - 202880

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 20M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 20MG

USFDA APPLICATION NUMBER - 202880

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 30M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 30MG

USFDA APPLICATION NUMBER - 202880

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 40M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 40MG

USFDA APPLICATION NUMBER - 202880

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 50M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 50MG

USFDA APPLICATION NUMBER - 202880

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DOSAGE - SOLUTION;ORAL - 4MG/5ML;5MG/5ML

USFDA APPLICATION NUMBER - 204307

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DOSAGE - SOLUTION;ORAL - 200MG/5ML;2.5MG/5ML

USFDA APPLICATION NUMBER - 205474

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DOSAGE - SOLUTION;ORAL - 200MG/5ML;2.5MG/5ML;...DOSAGE - SOLUTION;ORAL - 200MG/5ML;2.5MG/5ML;30MG/5ML

USFDA APPLICATION NUMBER - 22279

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DOSAGE - SOLUTION;ORAL - 4MG/5ML;5MG/5ML;60MG...DOSAGE - SOLUTION;ORAL - 4MG/5ML;5MG/5ML;60MG/5ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22439

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DOSAGE - SOLUTION;ORAL - 5MG/5ML;60MG/5ML **F...DOSAGE - SOLUTION;ORAL - 5MG/5ML;60MG/5ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22442

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DOSAGE - TABLET;ORAL - 1.5MG;5MG

USFDA APPLICATION NUMBER - 5213

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