LEVOMETHADYL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H29NO
Molecular Weight	311.4611
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=QIRAYNIFEOXSPW-PXNSSMCTSA-N

InChI=1S/C21H29NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17,20,23H,5,16H2,1-4H3/t17-,20-/m0/s1

HIDE SMILES / InChI

Approval Year

C_max

Value	Dose	Analyte	Population
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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

Doses

Dose	Population	Adverse 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 Health Status: unhealthy Age Group: 23 - 57 years Sex: M+F 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

AE	Significance	Dose	Population
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 Health Status: unhealthy Age Group: 23 - 57 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11760927/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C18 149 CYP2E1 729

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15104241/ Page: 7.0	minor
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15104241/ Page: 7.0	minor
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15104241/ Page: 7.0	minor
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15104241/ Page: 7.0	minor
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15104241/ Page: 7.0	minor
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15104241/ Page: 7.0	minor
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15104241/ Page: 7.0	minor
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15104241/ Page: 7.0	minor
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259570/;https://docs.boehringer-ingelheim.com/Prescribing%20Information/PIs/Roxane/Orlaam/Orlaam%20Oral%20Solution%2010mg%20per%20mL.pdf	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 Sources: https://pubmed.ncbi.nlm.nih.gov/11259570/;https://docs.boehringer-ingelheim.com/Prescribing%20Information/PIs/Roxane/Orlaam/Orlaam%20Oral%20Solution%2010mg%20per%20mL.pdf

Sourcing

Vendor/Aggregator	ID	URL
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

Name

Type

Language

(-)-.ALPHA.-METHADOL

Preferred Name

English

LEVOMETHADYL

Common Name

English

Levomethadyl [WHO-DD]

Common Name

English

(3S,6S)-METHADOL

Common Name

English

LEVOMETHADYL [VANDF]

Common Name

English

(-)-6-(DIMETHYLAMINO)-4,4-DIPHENYL-3-HEPTANOL

Systematic Name

English

Code System Code Type Description

CAS

14019-10-4