BENZHYDROCODONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H25NO4
Molecular Weight	403.4703
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]15CCN(C)[C@]([H])(C4)[C@]5([H])CC=C2OC(=O)C6=CC=CC=C6

InChI

InChIKey=VPMRSLWWUXNYRY-PJCFOSJUSA-N

InChI=1S/C25H25NO4/c1-26-13-12-25-17-9-11-20(29-24(27)15-6-4-3-5-7-15)23(25)30-22-19(28-2)10-8-16(21(22)25)14-18(17)26/h3-8,10-11,17-18,23H,9,12-14H2,1-2H3/t17-,18+,23-,25-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H25NO4
Molecular Weight	403.4703
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Benzhydrocodone is a prodrug of hydrocodone. Benzhydrocodone is formed by covalently bonding hydrocodone to benzoic acid. Benzhydrocodone itself is not pharmacologically active, but must be metabolized to hydrocodone by enzymes in the intestinal tract to optimally deliver its pharmacologic effects. Hydrocodone is a full agonist of the opioid receptors with a higher affinity for the mu-opioid receptor. Upon binding, hydrocodone produces an analgesic effect with no ceiling. APADAZ a combination of benzhydrocodone and acetaminophen is FDA approved and indicated for the short-term (no more than 14 days) management of acute pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate. APADAZ, even when taken as recommended, can result in addiction, abuse, and misuse, which can lead to overdose and death.

CNS Activity

Approval Year

Conditions

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614	Primary		Approved 8,429	ZOHYDRO ER
Acute pain 17	Primary		Approved 8,429	APADAZ

C_max

Value	Dose	Co-administered	Analyte	Population
13 ng/mL	15 mg single, oral		HYDROCODONE plasma	Homo sapiens
10.1 ng/mL	15 mg single, oral		HYDROCODONE plasma	Homo sapiens
23.6 ng/mL	10 mg single, oral		HYDROCODONE plasma	Homo sapiens
16.04 ng/mL	6.12 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
19.18 ng/mL	6.12 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
33.95 ng/mL	12.24 mg 6 times / day multiple, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
62.79 ng/mL	12.24 mg 6 times / day multiple, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
208 ng/mL	73.44 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
9.4 ng/mL	6.12 mg single, nasal	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
27 ng/mL	24.48 mg single, nasal	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
25.6 ng/mL	12.24 mg single, nasal		HYDROCODONE plasma	Homo sapiens
40.4 ng/mL	12.24 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
34.7 ng/mL	12.24 mg single, nasal	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
269 ng × h/mL	15 mg single, oral		HYDROCODONE plasma	Homo sapiens
155 ng × h/mL	15 mg single, oral		HYDROCODONE plasma	Homo sapiens
130.91 ng × h/mL	6.12 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
125.73 ng × h/mL	6.12 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
92.94 ng × h/mL	12.24 mg 6 times / day multiple, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
195.07 ng × h/mL	12.24 mg 6 times / day multiple, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
1272 ng × h/mL	73.44 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
194.7 ng × h/mL	12.24 mg single, nasal		HYDROCODONE plasma	Homo sapiens
252.7 ng × h/mL	12.24 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
278.3 ng × h/mL	12.24 mg single, nasal	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.5 h	15 mg single, oral		HYDROCODONE plasma	Homo sapiens
10.2 h	15 mg single, oral		HYDROCODONE plasma	Homo sapiens
4 h	10 mg single, oral		HYDROCODONE plasma	Homo sapiens
4.51 h	6.12 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
4.33 h	6.12 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
4.45 h	12.24 mg 6 times / day multiple, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
4.87 h	12.24 mg 6 times / day multiple, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
5 h	73.44 mg single, oral	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens
5.29 h	12.24 mg single, nasal		HYDROCODONE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
55%	10 mg single, oral		HYDROCODONE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
30 mg multiple, oral Overdose	unhealthy, 5 years	Other AEs: Adverse event...
160 mg 1 times / day multiple, oral Highest studied dose	unhealthy, adult	Other AEs: Electrocardiogram QTc interval prolonged...
20 mg 1 times / day multiple, oral Recommended	pregnant, adult	Other AEs: Withdrawal syndrome neonatal...
20 mg 1 times / day multiple, oral Recommended	unhealthy, adult	Other AEs: Respiratory depression, Addiction...
20 mg 1 times / day multiple, oral	unhealthy, adult	Disc. AE: Vomiting, Nausea...

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AEs

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AE	Significance	Dose	Population
Adverse event	grade 5	30 mg multiple, oral Overdose	unhealthy, 5 years
Electrocardiogram QTc interval prolonged		160 mg 1 times / day multiple, oral Highest studied dose	unhealthy, adult
Withdrawal syndrome neonatal		20 mg 1 times / day multiple, oral Recommended	pregnant, adult
Addiction		20 mg 1 times / day multiple, oral Recommended	unhealthy, adult
Respiratory depression	grade 5	20 mg 1 times / day multiple, oral Recommended	unhealthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737		substrate 1,217	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2B6 664 CYP2C19 991

Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP2B6 664	substrate 3,367	minor
CYP2C19 991	substrate 3,367	minor
CYP2D6 1,217	substrate 3,367	yes	yes (co-administration study)
CYP3A4 1,737	substrate 3,367	yes	yes (co-administration study)

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5779	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5779
eMolecules	29539213	https://www.emolecules.com/cgi-bin/more?vid=29539213
ZINC	ZINC000001280665	http://zinc15.docking.org/substances/ZINC000001280665

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PubMed

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Title	Date	PubMed
Efficacy and tolerability of celecoxib versus hydrocodone/acetaminophen in the treatment of pain after ambulatory orthopedic surgery in adults.	2001 Feb	11293556
Psychosis after ultrarapid opiate detoxification.	2001 Jun	11384923
Combination hydrocodone and ibuprofen versus combination oxycodone and acetaminophen in the treatment of moderate or severe acute low back pain.	2002 Jan	11833838
Simultaneous determination of hydrocodone and hydromorphone in human plasma by liquid chromatography with tandem mass spectrometric detection.	2002 Mar 25	11936695
Rational use of analgesic combinations.	2002 Oct	12436825

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Patents

Sample Use Guides

In Vivo Use Guide

APADAZ Immediate-release tablets: 6.12 mg benzhydrocodone (equivalent to 6.67 mg benzhydrocodone hydrochloride) and 325 mg acetaminophen. Initiate treatment with APADAZ at 1 or 2 tablets every 4 to 6 hours as needed for pain. Dosage should not exceed 12 tablets in a 24 hour period.

Route of Administration: Oral

Substance Class	Chemical
Record UNII	75MS0AAZ9I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZHYDROCODONE

Official Name

English

benzhydrocodone [INN]

Common Name

English

6,7-Didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6-yl benzoate

Systematic Name

English

MORPHINAN-6-OL, 6,7-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, 6-BENZOATE, (5.ALPHA.)-

Systematic Name

English

BENZHYDROCODONE [USAN]

Common Name

English

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Code System

Code

Type

Description

EVMPD

SUB182762

PRIMARY

INN

9897

PRIMARY

DRUG BANK

DB15465

PRIMARY

CAS

1259440-61-3

PRIMARY

DAILYMED

75MS0AAZ9I

PRIMARY

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Related Record

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BENZHYDROCODONE HYDROCHLORIDE

SALT/SOLVATE -> PARENT

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					6YKS4Y3WQ7

HYDROCODONE

METABOLITE ACTIVE -> PRODRUG

Amount:

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					6YKS4Y3WQ7

HYDROCODONE

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SMILES

InChI

CNS Activity

Approval Year

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound