naltrexone

Names

[ Name ]:
naltrexone

[Synonym ]:
Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-, (5α)-
Trexonil
NeMexin
(1S,5R,13R,17S)-4-(Cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0.0.0]octadeca-7(18),8,10-trien-14-on
Depotrex
ReVia
en1939
Naltrel
en1639
Naltrexone
Vivitrol
(5α)-17-(Cyclopropylmethyl)-3,14-dihydroxy-4,5-epoxymorphinan-6-one
Antaxone
trexan
(1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0.0.0]octadeca-7(18),8,10-trien-14-one
(1S,5R,13R,17S)-4-(cyclopropylméthyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0.0.0]octadéca-7(18),8,10-trién-14-one
celupan
En 1639A
Um-792
(5a)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one
Nalorex
Depade

Biological Activity

[Description]:

Naltrexone is an antagonist of Opioid receptor. Naltrexone inhibits cell proliferation in vivo. Naltrexone reduces tumor growth by interfering with cell signalling and modifying the immune system[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> GPCR/G Protein >> Opioid Receptor

Signaling Pathways >> Neuronal Signaling >> Opioid Receptor

[References]

[1]. Couto RD, et al. Low Doses Naltrexone: The Potential Benefit Effects for its Use in Patients with Cancer. Curr Drug Res Rev. 2021;13(2):86-89.

[2]. Lobmaier PP, et al. Naltrexone depot formulations for opioid and alcohol dependence: a systematic review. CNS Neurosci Ther. 2011 Dec;17(6):629-36.

[3]. Mannelli P, Peindl KS, Wu LT. Pharmacological enhancement of naltrexone treatment for opioid dependence: a review. Subst Abuse Rehabil. 2011 Jun;2011(2):113-123.

[4]. Swift R, Oslin DW, Alexander M, Forman R. Adherence monitoring in naltrexone pharmacotherapy trials: a systematic review. J Stud Alcohol Drugs. 2011 Nov;72(6):1012-8.

[5]. Makowski CT, Gwinn KM, Hurren KM. Naltrexone/bupropion: an investigational combination for weight loss and maintenance. Obes Facts. 2011;4(6):489-94.

[6]. Hulse GK. Improving Clinical Outcomes for Naltrexone as a Management of Problem Alcohol Use. Br J Clin Pharmacol. 2012 Sep 5. doi: 10.1111/j.1365-2125.2012.04452.x.

[7]. Naltrexone

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
558.1±50.0 °C at 760 mmHg

[ Melting Point ]:
168-170ºC

[ Molecular Formula ]:
C₂₀H₂₃NO₄

[ Molecular Weight ]:
341.40

[ Flash Point ]:
291.4±30.1 °C

[ Exact Mass ]:
341.162720

[ PSA ]:
70.00000

[ LogP ]:
1.80

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.709

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QD2155000

CHEMICAL NAME :: Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-alpha-epoxy-3,14-dihydroxy -

CAS REGISTRY NUMBER :: 16590-41-3

LAST UPDATED :: 199806

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C20-H23-N-O4

MOLECULAR WEIGHT :: 341.44

WISWESSER LINE NOTATION :: T B6566 B6/CO 4ABBC R BX FV HO PN GHT&&TTJ CQ JQ P1- AL3TJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 551 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1100 mg/kg

SEX/DURATION :: female 1-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - delayed effects

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 21 mg/kg

SEX/DURATION :: female 10-19 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Sex chromosome loss and nondisjunction

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 1 gm/L

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 1,180,1979

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

[ Hazard Codes ]:
F,T

[ Risk Phrases ]:
11-23/24/25-39/23/24/25

[ Safety Phrases ]:
16-36/37-45

[ RIDADR ]:
UN1230 - class 3 - PG 2 - Methanol, solution

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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