Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00364)
Name
Levorphanol
Synonyms    Click to Show/Hide the Synonyms of This API
levorphanol; Levorphan; Aromarone; Methorphinan; Racemethorphanum; Levo-Dromoran; Methorfinan [Czech]; Levorfanolo [DCIT]; Racemorphan; 17-Methylmorphinan-3-ol; Levorfanol [INN-Spanish]; Levorphanolum [INN-Latin]; Racemorfano [INN-Spanish]; Levorphanal; Ro 1-5431; DEA No. 9220; DEA No. 9733; L-morphan; (-)-3-Hydroxy-N-methylmorphinan; UNII-27618J1N2X; Morphinan-3-ol, 17-methyl-; Morphinan, 3-hydroxy-17-methyl-; Cetarin; Dromoran; CHEMBL592; Racemic dromoran; (-)-N-Methylmorphinan-3-ol; CHEBI:6444; LEVORPHANOL HYDROCHLORIDE; 77-07-6 (free); Orphan; 27618J1N2X; 297-90-5; Levorfanolo; Levorphanolum; Methorfinan; Racemorfano; Racemorphane; Racemorphanum; Levorfanol; N-Methyl-3-hydroxymorphinan; Racemorphan [INN:BAN]; 1,3,4,9,10,10a-Hexahydro-11-methyl-2H-10,4a-iminoethanophenanthren-6-ol, l-; 2H-10,4a-Iminoethanophenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-, l-; Racemorphane [INN-French]; Racemorphanum [INN-Latin]; Dextro-Dromoran; dl-3-Hydroxy-N-methylmorphinan; (+-)-17-Methylmorphinan-3-ol; (4bR,8aR,9R)-11-methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-3-ol; 2H-10,4a-Iminoethanophenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-; Levorphanol dl-form; Levorphanol (INN); NU 2206; HSDB 3349; (+-)-3-Hydroxy-N-methylmorphinan; Levorphanol [INN:BAN]; (+)-N-Methylmorphinan-3-ol; EINECS 201-002-6; EINECS 206-048-0; (+-)-N-Methylmorphinan-3-ol; Morphinan, 3-hydroxy-N-methyl, (+)-; 1,3,4,9,10,10a-Hexahydro-11-methyl-2H-10,4a-iminoethanophenanthren-6-ol, dl-mixture; d-Form of levorphanol; Morphinan-3-ol, 17-methyl-, (-)-; LEVORPHANOL-tartarate; Morphinan-3-ol, 17-methyl-, (+-)-; Morphinan, 3-hydroxy-N-methyl-, (+-)-; 2H-10, 4a-Iminoethanophenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-, dl-; SCHEMBL24335; GTPL7595; IDS-NL-007; DTXSID3023213; BDBM82427; (+)-cis-1,3,4,9,10,10a-Hexahydro-11-methyl-2H-10,4a-iminoethanophenanthren-6-ol; (-) 3-hydroxy-N-methylmorphinan; 2H-10,4a-(Iminoethano)phenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-, (+)-; BDBM224028; DTXSID301016136; ZINC3812984; BDBM50017233; BDBM50369518; 17-Methylmorphinan-3-ol, (+)- #; DB00854; CAS_5985-38-6; C08014; D08123; Q2579108; UNII-V7R79HN3XD component JAQUASYNZVUNQP-USXIJHARSA-N; 9.alpha.,13.alpha.,14.alpha.-Morphinan-3-ol, 17-methyl-; Morphinan-3-ol, 17-methyl-, (9.alpha.,13.alpha.,14.alpha.)-; (1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-4-ol
Clinical Status
Approved
Disease Indication Cerebral stroke ICD-11: 8B11 [1]
PubChem CID
5359272
Formula
C17H23NO
Canonical SMILES
CN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(C=C4)O
InChI
1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1
InChIKey
JAQUASYNZVUNQP-USXIJHARSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5359272"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 257.37 Topological Polar Surface Area 23.5
XlogP 3.1 Complexity 357
Heavy Atom Count 19 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Levorphanol 2 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose; Talc; Corn starch
                   Dosage Form Oral Tablet
                   Company Valeant Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Anhydrous lactose; Magnesium stearate; Starch, corn
                   Dosage Form Oral Tablet
                   Company Roxane Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 Levorphanol: revisiting an underutilized analgesic. Palliat Care. 2014 May 11;8:7-10.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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