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	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	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	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 2662	0.21 nM [Ki]
Delta opioid receptor 78 Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17039381	Agonist 2662	4.2 nM [Ki]
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17039381	Agonist 2662	2.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 608 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/074278.PDF	Palliative		Approved 8360	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 -5.3585281E11

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1709 inhibitor 1579		substrate 1193 inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1875	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes [IC50 11.5 uM]
CYP3A4 1909	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes [IC50 >50 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1193	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes
CYP3A4 1709	substrate 3326 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
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.	1995 Sep	7562497
Age-related differences in sensitivity to the antinociceptive effects of opioids in male rats. Influence of nociceptive intensity and intrinsic efficacy at the mu receptor.	2001 Aug	11498722
The safety of dextromethorphan in pregnancy : results of a controlled study.	2001 Feb	11171724
Clinical pharmacology of opioids for pain.	2002 Jul-Aug	12479250
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
The competitive N-methyl-D-aspartate receptor antagonist (-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid (LY235959) potentiates the antinociceptive effects of opioids that vary in efficacy at the mu-opioid receptor.	2003 Nov	12975489
10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors.	2004 Jan 1	14695830
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.	2005 Oct	16419411
Levorphanol revisited.	2007 Dec	18095794
Current aproach to cancer pain management: Availability and implications of different treatment options.	2007 Jun	18488078
Levorphanol: the forgotten opioid.	2007 Mar	17039381
High-affinity carbamate analogues of morphinan at opioid receptors.	2007 Mar 15	17276685
Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.	2007 May 31	17488103
Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A.	2007 Oct 26	17897634
Opiates and elderly: use and side effects.	2008	18686750
A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients.	2009 Jun 30	19566952
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.	2010 Jan	19797609
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 `Wed Jul 05 23:03:24 UTC 2023` Edited by `admin` on `Wed Jul 05 23:03:24 UTC 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