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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H31NO2.ClH
Molecular Weight 389.959
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOMETHADYL ACETATE HYDROCHLORIDE

SMILES

Cl.CC[C@H](OC(C)=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=UXBPQRGCVJOTNT-COBSGTNCSA-N
InChI=1S/C23H31NO2.ClH/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21;/h7-16,18,22H,6,17H2,1-5H3;1H/t18-,22-;/m0./s1

HIDE SMILES / InChI
Molecular Formula C23H31NO2
Molecular Weight 353.4977
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

1993
136
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
139 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15380290
80 mg 1 times / 2 days steady-state, oral
dose: 80 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DINORACETYLMETHADOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
184 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15380290
80 mg 1 times / 2 days steady-state, oral
dose: 80 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NORACYMETHADOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
188 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15380290
80 mg 1 times / 2 days steady-state, oral
dose: 80 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LEVOMETHADYL ACETATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5892 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15380290
80 mg 1 times / 2 days steady-state, oral
dose: 80 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DINORACETYLMETHADOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
6056 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15380290
80 mg 1 times / 2 days steady-state, oral
dose: 80 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NORACYMETHADOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2995 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15380290
80 mg 1 times / 2 days steady-state, oral
dose: 80 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LEVOMETHADYL ACETATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3 mg/kg multiple, oral
Studied dose
Dose: 3 mg/kg
Route: oral
Route: multiple
Dose: 3 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11760927/
unhealthy, 23 - 57 years
n = 6
Health Status: unhealthy
Condition: heroin dependency
Age Group: 23 - 57 years
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/11760927/
Disc. AE: Cardiotoxicity...
AEs leading to
discontinuation/dose reduction:
Cardiotoxicity (6 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11760927/
AEs

AEs

AESignificanceDosePopulation
Cardiotoxicity 6 patients
Disc. AE
3 mg/kg multiple, oral
Studied dose
Dose: 3 mg/kg
Route: oral
Route: multiple
Dose: 3 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11760927/
unhealthy, 23 - 57 years
n = 6
Health Status: unhealthy
Condition: heroin dependency
Age Group: 23 - 57 years
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/11760927/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737
substrate
1037
substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1054

CYP2A6
543

CYP2B6
664

CYP2C8
693

CYP2C18
138

CYP2E1
667
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1054
 minor
CYP2A6
543
 minor
CYP2B6
664
 minor
CYP2C18
138
 minor
CYP2C8
693
 minor
CYP2C9
1037
 minor
CYP2D6
1217
 minor
CYP2E1
667
 minor
CYP3A4
1737
 yes
likely (co-administration study)
Comment: the addition of drugs that induce this enzyme (such as rifampin, phenobarbital, and phenytoin) or inhibit this enzyme (such as ketoconazole, erythromycin, and saquinavir) could increase the levels of parent drug or its active metabolites in a patient that was previously at steady-state, and this could potentially precipitate serious arrhythmias, including torsade de pointes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ABI Chem
AC1L21LS
Ambinter
Amb22336843
http://www.ambinter.com/reference/22336843
Aurora Fine Chemicals LLC
A17.900.919
http://online.aurorafinechemicals.com/info?ID=A17.900.919
Chemieliva Pharmaceutical Co., Ltd
PBCM1306631
Glentham Life Sciences
GL4015
http://www.glentham.com/products/product/GL4015/
NovoSeek
39371
PubChem
39371
https://pubchem.ncbi.nlm.nih.gov/compound/39371
Sigma-Aldrich
L7418_SIGMA
https://www.sigmaaldrich.com/catalog/product/sigma/l7418?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule
S532971
http://www.smolecule.com/products/s532971
THE BioTek
bt-273431
https://www.thebiotek.com/product/inhibitors/bt-273431
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:14:21 UTC 2023
Edited
by admin
on Fri Dec 15 15:14:21 UTC 2023
Record UNII
B54CW5KG52
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMETHADYL ACETATE HYDROCHLORIDE
MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
LEVACETYLMETHADOL HYDROCHLORIDE [MART.]
Common Name English
MK790
Code English
LEVOMETHADYL ACETATE HYDROCHLORIDE [MI]
Common Name English
ORLAAM
Brand Name English
LEVOMETHADYL ACETATE HCL
Common Name English
LEVOMETHADYL ACETATE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
MK-790
Code English
LEVOMETHADYL ACETATE HYDROCHLORIDE [USAN]
Common Name English
BENZENEETHANOL, .BETA.-(2-(DIMETHYLAMINO)PROPYL)-.ALPHA.-ETHYL-.BETA.-PHENYL-, ACETATE (ESTER), HYDROCHLORIDE, (S-(R*,R*))-
Common Name English
LEVOMETHADYL ACETATE HYDROCHLORIDE [VANDF]
Common Name English
(-)-(3S,6S)-6-(DIMETHYLAMINO)-4,4-DIPHENYL-3-HEPTANOL ACETATE (ESTER), HYDROCHLORIDE
Common Name English
Levomethadyl acetate hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
FDA ORPHAN DRUG 4784
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
NCI_THESAURUS C1506
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
Code System Code Type Description
CAS
43033-72-3
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
WIKIPEDIA
Levomethadyl acetate hydrochloride
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
DRUG BANK
DBSALT001444
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
SMS_ID
100000089116
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL1514
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
RXCUI
82043
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C47583
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
CHEBI
6441
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
USAN
GG-23
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
MERCK INDEX
m6789
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY Merck Index
FDA UNII
B54CW5KG52
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID7020500
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
PUBCHEM
39371
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
EVMPD
SUB14353MIG
Created by admin on Fri Dec 15 15:14:21 UTC 2023 , Edited by admin on Fri Dec 15 15:14:21 UTC 2023
PRIMARY
Related Record Type Details
Structure of LEVOMETHADYL ACETATE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of LEVOMETHADYL
ACTIVE MOIETY
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