Details of the Drug

General Information of Drug (ID: DMGS80V)

Drug Name

Levorphanol

Synonyms

levorphanol; Levorphan; Methorphinan; Aromarone; Racemethorphanum; Dromoran; Cetarin; Antalgin; Levo-Dromoran; Racemic dromoran; Methorfinan [Czech]; Levorfanolo [DCIT]; Levorphanolum; Levorfanol; Orphan; Levorfanol [INN-Spanish]; Levorphanolum [INN-Latin]; Racemorfano [INN-Spanish]; 17-Methylmorphinan-3-ol; N-Methyl-3-hydroxymorphinan; Racemorphan; Racemorphan [INN:BAN]; Racemorphane [INN-French]; Racemorphanum [INN-Latin]; (-)-N-Methylmorphinan-3-ol; Morphinan-3-ol, 17-methyl-; Levorphanal; dl-3-Hydroxy-N-methylmorphinan; DEA No; Antalgin; DEXTRORPHAN; Levodroman; Levorfanolo; Methorfinan; Racemorfano; Racemorphane; Racemorphanum; NU 2206; L-Dromoran; Levorphanol (INN); Ro 1-5431; Levo-Dromoran (TN); Dl-3-Hydroxy-N-methylmorphinan; (+)-3-Hydroxy-17-methylmorphinan; (+-)-17-Methylmorphinan-3-ol; (+-)-3-Hydroxy-N-methylmorphinan; (-)-3-Hydroxy-N-methylmorphinan; 1,3,4,9,10,10a-Hexahydro-11-methyl-2H-10,4a-iminoethanophenanthren-6-ol, dl-mixture; 1,3,4,9,10,10a-Hexahydro-6-hydroxy-2H-10,4a-(iminoethano)-11-methylphenanthrene; 3-Hydroxy-N-methylmorphinan; Dextrorphan

Indication

Disease Entry	ICD 11	Status	REF
Pain	MG30-MG3Z	Approved	[1]
Ischemic stroke	8B11.5Z	Terminated	[2]
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Therapeutic Class

Analgesics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

257.37

Logarithm of the Partition Coefficient (xlogp)

3.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Clearance: The clearance of drug is 0.78 to 1.1 L/h/kg []
Half-life: The concentration or amount of drug in body reduced by one-half in 11 - 16 hours [3]
Metabolism: The drug is metabolized via the liver []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.5828 micromolar/kg/day [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.6% [3]
Vd: The volume of distribution (Vd) of drug is 10-13 L/kg []

Chemical Identifiers

Formula: C17H23NO
IUPAC Name: (1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
Canonical SMILES: CN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(C=C4)O
InChI: 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

Cross-matching ID

PubChem CID: 5359272
ChEBI ID: CHEBI:6444
CAS Number: 297-90-5
DrugBank ID: DB00854
TTD ID: D0T3HY
ACDINA ID: D00364

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
N-methyl-D-aspartate receptor (NMDAR)	TT9IK2Z	NOUNIPROTAC	Antagonist	[5]
Opioid receptor (OPR)	TTN4QDT	NOUNIPROTAC	Agonist	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Levorphanol

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Oxymorphone	DM65AGJ	Major	Additive CNS depression effects by the combination of Levorphanol and Oxymorphone.	Pain [MG30-MG3Z]	[7]
Dezocine	DMJDB0Y	Major	Additive CNS depression effects by the combination of Levorphanol and Dezocine.	Pain [MG30-MG3Z]	[8]
Flavoxate	DMKV4NL	Moderate	Additive antimotility effects by the combination of Levorphanol and Flavoxate.	Pain [MG30-MG3Z]	[9]
Buprenorphine	DMPRI8G	Major	Additive CNS depression effects by the combination of Levorphanol and Buprenorphine.	Pain [MG30-MG3Z]	[8]
Hydrocodone	DMQ2JO5	Major	Additive CNS depression effects by the combination of Levorphanol and Hydrocodone.	Pain [MG30-MG3Z]	[7]
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Coadministration of a Drug Treating the Disease Different from Levorphanol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Oliceridine	DM6MDCF	Major	Additive CNS depression effects by the combination of Levorphanol and Oliceridine.	Acute pain [MG31]	[7]
Chlormezanone	DMTWUXR	Major	Additive CNS depression effects by the combination of Levorphanol and Chlormezanone.	Anxiety disorder [6B00-6B0Z]	[7]
Desipramine	DMT2FDC	Moderate	Additive CNS depression effects by the combination of Levorphanol and Desipramine.	Attention deficit hyperactivity disorder [6A05]	[10]
Cariprazine	DMJYDVK	Major	Additive CNS depression effects by the combination of Levorphanol and Cariprazine.	Bipolar disorder [6A60]	[7]
Dihydrocodeine	DMB0FWL	Major	Additive CNS depression effects by the combination of Levorphanol and Dihydrocodeine.	Chronic pain [MG30]	[11]
Levomilnacipran	DMV26S8	Moderate	Additive serotonergic effects by the combination of Levorphanol and Levomilnacipran.	Chronic pain [MG30]	[10]
Ethanol	DMDRQZU	Moderate	Additive CNS depression effects by the combination of Levorphanol and Ethanol.	Cystitis [GC00]	[12]
Cyclobenzaprine	DM1YBRM	Major	Additive CNS depression effects by the combination of Levorphanol and Cyclobenzaprine.	Depression [6A70-6A7Z]	[7]
Vilazodone	DM4LECQ	Moderate	Additive serotonergic effects by the combination of Levorphanol and Vilazodone.	Depression [6A70-6A7Z]	[10]
Nefazodone	DM4ZS8M	Moderate	Additive serotonergic effects by the combination of Levorphanol and Nefazodone.	Depression [6A70-6A7Z]	[10]
Vortioxetine	DM6F1PU	Moderate	Additive CNS depression effects by the combination of Levorphanol and Vortioxetine.	Depression [6A70-6A7Z]	[10]
Milnacipran	DMBFE74	Moderate	Additive serotonergic effects by the combination of Levorphanol and Milnacipran.	Depression [6A70-6A7Z]	[10]
Escitalopram	DMFK9HG	Moderate	Additive CNS depression effects by the combination of Levorphanol and Escitalopram.	Depression [6A70-6A7Z]	[10]
Desvenlafaxine	DMHD4PE	Moderate	Additive CNS depression effects by the combination of Levorphanol and Desvenlafaxine.	Depression [6A70-6A7Z]	[10]
OPC-34712	DMHG57U	Major	Additive CNS depression effects by the combination of Levorphanol and OPC-34712.	Depression [6A70-6A7Z]	[7]
Clomipramine	DMINRKW	Moderate	Additive CNS depression effects by the combination of Levorphanol and Clomipramine.	Depression [6A70-6A7Z]	[10]
Doxepin	DMPI98T	Moderate	Additive serotonergic effects by the combination of Levorphanol and Doxepin.	Depression [6A70-6A7Z]	[10]
Maprotiline	DMPWB7T	Moderate	Additive serotonergic effects by the combination of Levorphanol and Maprotiline.	Depression [6A70-6A7Z]	[10]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Levorphanol and Esketamine.	Depression [6A70-6A7Z]	[13]
Mepenzolate	DM8YU2F	Moderate	Additive CNS depression effects by the combination of Levorphanol and Mepenzolate.	Digestive system disease [DE2Z]	[9]
5-hydroxy-L-tryptophan	DMDWZGJ	Moderate	Additive serotonergic effects by the combination of Levorphanol and 5-hydroxy-L-tryptophan.	Discovery agent [N.A.]	[10]
Oxybutynine	DMJPBAX	Moderate	Additive CNS depression effects by the combination of Levorphanol and Oxybutynine.	Discovery agent [N.A.]	[9]
Heroin diacetylmorphine	DMDBWHY	Major	Additive CNS depression effects by the combination of Levorphanol and Heroin diacetylmorphine.	Dissociative neurological symptom disorder [6B60]	[11]
Gabapentin	DM6T924	Major	Additive CNS depression effects by the combination of Levorphanol and Gabapentin.	Epilepsy/seizure [8A61-8A6Z]	[14]
Clonazepam	DMTO13J	Major	Additive CNS depression effects by the combination of Levorphanol and Clonazepam.	Epilepsy/seizure [8A61-8A6Z]	[7]
Phenobarbital	DMXZOCG	Major	Additive CNS depression effects by the combination of Levorphanol and Phenobarbital.	Epilepsy/seizure [8A61-8A6Z]	[7]
Dantrolene	DM1D8XY	Major	Additive CNS depression effects by the combination of Levorphanol and Dantrolene.	Fever [MG26]	[7]
Solifenacin	DMG592Q	Moderate	Additive CNS depression effects by the combination of Levorphanol and Solifenacin.	Functional bladder disorder [GC50]	[9]
Tolterodine	DMSHPW8	Moderate	Additive CNS depression effects by the combination of Levorphanol and Tolterodine.	Functional bladder disorder [GC50]	[9]
Belladonna	DM2RBWK	Moderate	Additive antimotility effects by the combination of Levorphanol and Belladonna.	Infectious gastroenteritis/colitis [1A40]	[9]
Suvorexant	DM0E6S3	Major	Additive CNS depression effects by the combination of Levorphanol and Suvorexant.	Insomnia [7A00-7A0Z]	[7]
Amobarbital	DM0GQ8N	Major	Additive CNS depression effects by the combination of Levorphanol and Amobarbital.	Insomnia [7A00-7A0Z]	[7]
Ramelteon	DM7IW9J	Major	Additive CNS depression effects by the combination of Levorphanol and Ramelteon.	Insomnia [7A00-7A0Z]	[7]
Triazolam	DMETYK5	Major	Additive CNS depression effects by the combination of Levorphanol and Triazolam.	Insomnia [7A00-7A0Z]	[7]
Zaleplon	DMGFWSM	Major	Additive CNS depression effects by the combination of Levorphanol and Zaleplon.	Insomnia [7A00-7A0Z]	[7]
Tasimelteon	DMLOQ1V	Major	Additive CNS depression effects by the combination of Levorphanol and Tasimelteon.	Insomnia [7A00-7A0Z]	[7]
Paraldehyde	DMOC1BX	Major	Additive CNS depression effects by the combination of Levorphanol and Paraldehyde.	Insomnia [7A00-7A0Z]	[7]
ITI-007	DMUQ1DO	Major	Additive CNS depression effects by the combination of Levorphanol and ITI-007.	Insomnia [7A00-7A0Z]	[7]
Quazepam	DMY4D87	Major	Additive CNS depression effects by the combination of Levorphanol and Quazepam.	Insomnia [7A00-7A0Z]	[7]
Estazolam	DMZGXUM	Major	Additive CNS depression effects by the combination of Levorphanol and Estazolam.	Insomnia [7A00-7A0Z]	[7]
Polyethylene glycol	DM4I1JP	Moderate	Increased risk of lowers seizure threshold by the combination of Levorphanol and Polyethylene glycol.	Irritable bowel syndrome [DD91]	[15]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Levorphanol and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[16]
Almogran	DM7I64Z	Moderate	Additive CNS depression effects by the combination of Levorphanol and Almogran.	Migraine [8A80]	[10]
Frovatriptan	DM7RE8P	Moderate	Additive CNS depression effects by the combination of Levorphanol and Frovatriptan.	Migraine [8A80]	[10]
Rizatriptan	DMDJMA3	Moderate	Additive serotonergic effects by the combination of Levorphanol and Rizatriptan.	Migraine [8A80]	[10]
Naratriptan	DMO50U2	Moderate	Additive serotonergic effects by the combination of Levorphanol and Naratriptan.	Migraine [8A80]	[10]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Levorphanol and Lasmiditan.	Migraine [8A80]	[17]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Levorphanol and Flibanserin.	Mood disorder [6A60-6E23]	[18]
Thalidomide	DM70BU5	Moderate	Additive CNS depression effects by the combination of Levorphanol and Thalidomide.	Multiple myeloma [2A83]	[19]
Prasugrel	DM7MT6E	Moderate	Altered absorption of Levorphanol due to GI dynamics variation caused by Prasugrel.	Myocardial infarction [BA41-BA43]	[20]
Granisetron	DMIUW25	Moderate	Additive CNS depression effects by the combination of Levorphanol and Granisetron.	Nausea/vomiting [MD90]	[10]
Ondansetron	DMOTQ1I	Moderate	Additive serotonergic effects by the combination of Levorphanol and Ondansetron.	Nausea/vomiting [MD90]	[10]
Bupropion	DM5PCS7	Major	Increased risk of lowers seizure threshold by the combination of Levorphanol and Bupropion.	Nicotine use disorder [6C4A]	[21]
Sibutramine	DMFJTDI	Moderate	Additive serotonergic effects by the combination of Levorphanol and Sibutramine.	Obesity [5B80-5B81]	[10]
Dexfenfluramine	DMJ7YDS	Moderate	Additive serotonergic effects by the combination of Levorphanol and Dexfenfluramine.	Obesity [5B80-5B81]	[10]
Levomethadyl Acetate	DM06HG5	Major	Additive CNS depression effects by the combination of Levorphanol and Levomethadyl Acetate.	Opioid use disorder [6C43]	[11]
Apraclonidine	DMO4PVE	Moderate	Additive CNS depression effects by the combination of Levorphanol and Apraclonidine.	Optic nerve disorder [9C40]	[22]
Pimavanserin	DMR7IVC	Major	Additive CNS depression effects by the combination of Levorphanol and Pimavanserin.	Parkinsonism [8A00]	[7]
Orphenadrine	DMW542E	Major	Additive CNS depression effects by the combination of Levorphanol and Orphenadrine.	Parkinsonism [8A00]	[7]
Methylscopolamine	DM5VWOB	Moderate	Additive CNS depression effects by the combination of Levorphanol and Methylscopolamine.	Peptic ulcer [DA61]	[9]
Quetiapine	DM1N62C	Major	Additive CNS depression effects by the combination of Levorphanol and Quetiapine.	Schizophrenia [6A20]	[23]
Aripiprazole	DM3NUMH	Major	Additive CNS depression effects by the combination of Levorphanol and Aripiprazole.	Schizophrenia [6A20]	[7]
Iloperidone	DM6AUFY	Major	Additive CNS depression effects by the combination of Levorphanol and Iloperidone.	Schizophrenia [6A20]	[7]
Paliperidone	DM7NPJS	Major	Additive CNS depression effects by the combination of Levorphanol and Paliperidone.	Schizophrenia [6A20]	[7]
Molindone	DMAH70G	Major	Additive CNS depression effects by the combination of Levorphanol and Molindone.	Schizophrenia [6A20]	[7]
Thiothixene	DMDINC4	Major	Additive CNS depression effects by the combination of Levorphanol and Thiothixene.	Schizophrenia [6A20]	[23]
Asenapine	DMSQZE2	Major	Additive CNS depression effects by the combination of Levorphanol and Asenapine.	Schizophrenia [6A20]	[7]
Pimozide	DMW83TP	Major	Additive CNS depression effects by the combination of Levorphanol and Pimozide.	Schizophrenia [6A20]	[7]
Brilinta	DMBR01X	Moderate	Altered absorption of Levorphanol due to GI dynamics variation caused by Brilinta.	Thrombosis [DB61-GB90]	[20]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Levorphanol 2 mg tablet	2 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800009336)
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Neuroprotective agents for the treatment of acute ischemic stroke. Curr Neurol Neurosci Rep. 2003 Jan;3(1):9-20.
6	Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis. J Pharmacol Exp Ther. 2004 May;309(2):515-22.
7	US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
8	Product Information. Buprenex (buprenorphine). Reckitt and Colman Pharmaceutical, Richmond, VA.
9	Product Information. Apadaz (acetaminophen-benzhydrocodone). KemPharm, Inc, Coralville, IA.
10	Vizcaychipi MP, Walker S, Palazzo M "Serotonin syndrome triggered by tramadol." Br J Anaesth 99 (2007): 919. [PMID: 18006535]
11	US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
12	Sturner WQ, Garriott JC "Deaths involving propoxyphene: a study of 41 cases over a two-year period." JAMA 223 (1973): 1125-30. [PMID: 4739371]
13	Cerner Multum, Inc. "Australian Product Information.".
14	Eckhardt K, Ammon S, Hofmann U, Riebe A, Gugeler N, Mikus G "Gabapentin enhances the analgesic effect of morphine in healthy volunteers." Anesth Analg 91 (2000): 185-91. [PMID: 10866910]
15	Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
16	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
17	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
18	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
19	Product Information. Thalomid (thalidomide). Celgene Corporation, Warren, NJ.
20	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
21	Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.
22	Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.
23	Cerner Multum, Inc. "Canadian Product Information.".