LEVORPHANOL TARTRATE

First approved in 1953

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H23NO.C4H6O6.2H2O
Molecular Weight	443.488
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.O[C@H]([C@@H](O)C(O)=O)C(O)=O.[H][C@@]12CCCC[C@@]13CCN(C)[C@@H]2CC4=C3C=C(O)C=C4

InChI

InChIKey=UMZNDVASJKIQCB-QLFXFZCRSA-N

InChI=1S/C17H23NO.C4H6O6.2H2O/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17;5-1(3(7)8)2(6)4(9)10;;/h5-6,11,14,16,19H,2-4,7-10H2,1H3;1-2,5-6H,(H,7,8)(H,9,10);2*1H2/t14-,16+,17+;1-,2-;;/m01../s1

HIDE SMILES / InChI

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C17H23NO
Molecular Weight	257.3706
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/pro/levorphanol.html | https://www.ncbi.nlm.nih.gov/pubmed/17039381

Levorphanol, brand name Levo-Dromoran, is an opioid medication used to treat moderate to severe pain. Levorphanol is indicated for the management of moderate to severe pain where an opioid analgesic is appropriate. It is a potent synthetic opioid mu-receptor agonist similar in action to morphine. Like other opioid mu-receptor agonists, it is believed to act at receptors in both the brain and spinal cord to alter the transmission and perception of pain. The onset and peak analgesic effects following administration of levorphanol are similar to morphine when administered at equal analgesic doses. Levorphanol produces a degree of respiratory depression similar to that produced by morphine at equal analgesic doses, and like many opioid mu-receptor agonists, levorphanol produces euphoria or has a positive effect on mood in many individuals.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17039381 \| https://www.ncbi.nlm.nih.gov/pubmed/17276685	Agonist 2678	0.21 nM [Ki]
Delta opioid receptor 77 Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17039381	Agonist 2678	4.2 nM [Ki]
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17039381	Agonist 2678	2.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/074278.PDF	Palliative		Approved 8429	Levorphanol Tartrate Approved Use Levorphanol Tartrate Tablets are indicated for the management of pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate. Launch Date 1953

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587		substrate 1217 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes [IC50 11.5 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes [IC50 >50 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes

Sourcing

Vendor/Aggregator	ID	URL
AAA Chemistry	AR-1E1926
ABI Chem	AC1L1H05
ABI Chem	AC1Q7AI1
AHH Chemical co.,ltd	MT-53063	http://www.ahhchemical.com/product/MT-53063.html
BOC Sciences	125-73-5	https://www.bocsci.com/dextromethorphan-ep-impurity-b-dextrorphan-cas-125-73-5-item-470048.html
BioChemPartner	BCP24334	http://www.biochempartner.com/125-73-5-BCP24334
Clearsynth	CS-O-16970	https://www.clearsynth.com/en/CSO16970.html
Compound Cloud	5359272
Compound Cloud	5462348
HongKong Chemhere	SCA54099
MuseChem	I014442
NovoSeek	3918
NovoSeek	5390113
Smolecule	S532999	http://www.smolecule.com/products/s532999
THE BioTek	bt-272670	https://www.thebiotek.com/product/inhibitors/bt-272670
Tetrahedron	TS81326
Toronto Research Chemicals	KIT8295
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0703A
ZINC	ZINC000003812984	http://zinc15.docking.org/substances/ZINC000003812984
eMolecules	261267554
eMolecules	48858227

PubMed

Title	Date	PubMed
Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys.	1981	6794076
Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates.	1982 Jan	6278540
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine.	1984	6543399
Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence.	1984 Jun 25	6146083
Baclofen-induced catatonia.	1986 Dec	3805341
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.	1991 Mar-Apr	1685312
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.	1995 Sep	7562497
Central discriminative effects of morphine in rats: training via intracerebroventricular administration.	2001 Dec	11786240
Pitfalls of opioid rotation: substituting another opioid for methadone in patients with cancer pain.	2002 Apr	11973005
Interface for coupling nonaqueous wide-bore capillary electrophoresis with mass spectrometry.	2002 Feb	11870745
Antidepressant-like effects of tramadol and other central analgesics with activity on monoamines reuptake, in helpless rats.	2002 Nov 29	12417248
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.	2003 Aug	12709780
Opioids and chronic neuropathic pain.	2003 Mar 27	12660393
Oral opioid therapy for chronic peripheral and central neuropathic pain.	2003 Mar 27	12660386
Differential regulation of the human kappa opioid receptor by agonists: etorphine and levorphanol reduced dynorphin A- and U50,488H-induced internalization and phosphorylation.	2003 May	12606694
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization.	2005 Jul	15843500
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.	2005 Oct	16419411
Opioid peptides and receptors in joint tissues: study in the rat.	2006 Jun	16649179
Role of atypical opiates in OCD. Experimental approach through the study of 5-HT(2A/C) receptor-mediated behavior.	2007 Feb	17102981
The effect of opiates on the activity of human placental aromatase/CYP19.	2007 Jan 15	17118343
Morphine reduces local cytokine expression and neutrophil infiltration after incision.	2007 Oct 2	17908329
An evaluation of the genotoxicity of the antitussive drug Dextromethorphan.	2008 Apr	18160193
Challenges in using opioids to treat pain in persons with substance use disorders.	2008 Jun	18497713
Opioid pharmacology.	2008 Mar	18443637
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.	2009 Jul	20532104
Somatostatin and opioid receptors do not regulate proliferation or apoptosis of the human multiple myeloma U266 cells.	2009 Jun 7	19500423
Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor.	2009 Sep	19719367
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.	2010 Feb	20394254
Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: ligands for mu, kappa, and delta opioid receptors.	2010 Jan 14	19928862
Acute pain management in children.	2010 Jul 15	21197314

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Light Sedation Premedication for Anesthesia: 1 to 2 mg IM or subcutaneously, administered 60 to 90 minutes before surgery. Older or debilitated patients usually require less drug. Two mg of levorphanol is approximately equivalent to 10 to 15 mg of morphine or 100 mg of meperidine. Usual Adult Dose for Pain IV: 1 mg every 3 to 6 hours as needed. IM or subcutaneous: 1 to 2 mg every 6 to 8 hours as needed. Oral: 2 mg every 6 to 8 hours as needed. May be increased to 3 mg every 6 to 8 hours.

Route of Administration: Other

In Vitro Use Guide

Levorphanol (5-100 uM), consistently depressed the responses evoked by the putative inhibitory amino acid neurotransmitters glycine and beta-alanine but not GABA in cultured mouse spinal cord neurons.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:33:59 GMT 2023` Edited by `admin` on `Fri Dec 15 15:33:59 GMT 2023`
Record UNII	04WQU6T9QI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVORPHANOL TARTRATE

Common Name

English

RO-1-5431/7

Code

English

Levorphanol tartrate dihydrate [WHO-DD]

Common Name

English

LEVO-DROMORAN

Brand Name

English

17-Methylmorphinan-3-ol, tartrate (1:1) (salt) dihydrate

Common Name

English

LEVORPHANOL TARTRATE [MART.]

Common Name

English

LEVORPHANOL TARTRATE DIHYDRATE [MI]

Common Name

English

LEVORPHANOL TARTRATE [USP-RS]

Common Name

English

MORPHINAN-3-OL, 17-METHYL-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1) (SALT), DIHYDRATE

Common Name

English

LEVORPHANOL TARTRATE [USP MONOGRAPH]

Common Name

English

LEVORPHANOL TARTRATE [VANDF]

Common Name

English

LEVORPHANOL TARTRATE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1506