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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO.H2O4S
Molecular Weight 355.449
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVORPHANOL SULFATE

SMILES

OS(O)(=O)=O.[H][C@@]12CC3=C(C=C(O)C=C3)[C@]4(CCCC[C@@]14[H])CCN2C

InChI

InChIKey=AWSHMQGEXAEMGM-DYWKTHLTSA-N
InChI=1S/C17H23NO.H2O4S/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17;1-5(2,3)4/h5-6,11,14,16,19H,2-4,7-10H2,1H3;(H2,1,2,3,4)/t14-,16+,17+;/m0./s1

HIDE SMILES / InChI

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

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b2ab70e4-ca0c-4a73-9c98-974bf94e890c&type=display | https://www.ncbi.nlm.nih.gov/pubmed/12502358 | https://www.ncbi.nlm.nih.gov/pubmed/15055988

Levorphanol Sulfate (brand name Levo-Dromoran) is an opioid medication used to treat moderate to severe pain. It is one of two enantiomers of the compound racemorphan and was first described in Germany in 1948 and approved for use in the United States in 1953 as an orally active, morphine-like analgesic. Levorphanol is approved for use in moderate to severe pain where an opioid analgesic is appropriate. Levorphanol has a wide range of activities including mu-opioid agonism, delta agonism, kappa1 and kappa3 receptor agonism, N-methyl-D-aspartate receptor antagonism and reuptake inhibition of both norepinephrine and serotonin. This multimodal profile might prove effective for pain syndromes that are refractory to other opioid analgesics, such as central and neuropathic pain and opioid-induced hyperalgesia. Levorphanol is well suited as a first-line opioid and can also be used during opioid rotation. It has no known effect on the cardiac QT interval or drug-drug interactions involving hepatic cytochrome P450s enzymes. In these regards, levorphanol may offer a superior safety profile over methadone and other long-acting opioids. Despite its prospective value of multiple mechanisms of action and the potential for treating various types of pain, levorphanol use has been largely supplanted by other recently approved opioids. Its waning use over the years has caused it to be referred to as the “Forgotten Opioid” and resulted in what some consider its underutilization. In fact, levorphanol is relatively unfamiliar to most prescribers.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.13 nM [IC50]
2.3 nM [Ki]
4.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
levorphanol

Approved Use

INDICATIONS AND USAGE Levorphanol Tartrate Tablets USP are indicated for the management of moderate to severe pain where an opioid analgesic is appropriate.

Launch Date

9.578304E11
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

The usual recommended starting dose for oral administration is 2 mg. This may be repeated in 6 to 8 hours as needed, provided the patient is assessed for signs of hypoventilation and excessive sedation. If necessary, the dose may be increased to up to 3 mg every 6 to 8 hours, after adequate evaluation of the patient’s response. Higher doses may be appropriate in opioid tolerant patients.
Route of Administration: Oral
In Vitro Use Guide
Samples containing 100-125 mkg of Synaptic plasma membranes protein and the appropriate drug concentration were incubated in 2.0 ml of 100 mM Tria-HC1 buffer, pH 7.4, containing 0 .25-0.50 mkCi45 CaCl2 and concentrations of [45Ca]Cl2 ranging from 0 .1-1 .25 mkM. Incubations were performed at 37 ° C for 10 minutes in a Dubnoff Metabolic Shaker. Binding experiments involving displacement of [45Ca] previously bound to Synaptic plasma membranes had controls run for 20 minutes . Reactions were terminated by the addition of 5 ml of ice-cold Tris buffer followed by rapid filtration (5-7 sec) over Millipore filters (0 .45 uM) previously washed with 0.25 M KCl . Membranes were washed again with two, 5 ml batches of ice-cold Tris buffer (pH 7.4, 25 C) . The filters were removed, dried at 80 C and counted by liquid scintillation on a Searle Analytic Isocap 300. Results are expressed as picomolea of Cam bound per mg of synaptic protein . Slopes and intercepts of lines were determined by regression analysis using standard program packages for Monroe 325 calculator . Levorphanol (0.5-10nM) inhibits Ca2+ binding to synaptic membranes in a dose dependent fashion
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:15:10 UTC 2023
Edited
by admin
on Sat Dec 16 10:15:10 UTC 2023
Record UNII
RST9EKW39R
Record Status Validated (UNII)
Record Version
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Name Type Language
LEVORPHANOL SULFATE
Common Name English
MORPHINAN-3-OL, 17-METHYL-, SULFATE (SALT)
Systematic Name English
Code System Code Type Description
CAS
61095-53-2
Created by admin on Sat Dec 16 10:15:10 UTC 2023 , Edited by admin on Sat Dec 16 10:15:10 UTC 2023
PRIMARY
PUBCHEM
66686930
Created by admin on Sat Dec 16 10:15:10 UTC 2023 , Edited by admin on Sat Dec 16 10:15:10 UTC 2023
PRIMARY
FDA UNII
RST9EKW39R
Created by admin on Sat Dec 16 10:15:10 UTC 2023 , Edited by admin on Sat Dec 16 10:15:10 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE