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(-)-Phenserine

(-)-Phenserine structure

CAS No:
101246-66-6
Formula:
C20H23N3O2
Chemical Name:
(-)-Phenserine
Synonyms:
Pyrrolo[2,3-b]indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-,5-(N-phenylcarbamate),(3aS,8aR)-;Pyrrolo[2,3-b]indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-,phenylcarbamate (ester),(3aS-cis)-;Pyrrolo[2,3-b]indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-,phenylcarbamate (ester),(3aS,8aR)-;Phenserine;(-)-Eseroline phenylcarbamate;(-)-Phenserine;(-)-N-Phenylcarbamoyleseroline
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

Phenserine is under development by Axonyx, a US biopharmaceutical company that focuses on treatments for dementia. Phenserine is a next generation acetylcholinesterase (AChE) inhibitor indicated for the treatment of AD. Unlike currently marketed AChE inhibitors, it has a dual mechanism of action that also includes anti-amyloid activity, which may confer disease-modifying effects in patients with AD. If this is substantiated in an ongoing clinical trial then phenserine may open the door to an entirely new type of treatment for AD. Axonyx announced on 20 September 2005 that phenserine was ineffective in two curtailed phase 3 trials.

(-)-Phenserine Basic Attributes

Molecular Weight：

337.4 g/mol

Exact Mass：

337.42

UNII：

SUE285UG3S

Characteristics

PSA：

44.8 Å²

Melting Point：

151-152 °C

Safety Information

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

The toxicity of phenserine, a derivate of physostigmine, is dramatically less. Doses of 20 mg/kg (rats, intravenous) of phenserine have not been associated with toxicity or deaths.

Drug Information

Drug Indication：

For the treatment of Alzheimer's disease (AD).

Pharmacology：

Phenserine, a phenylcarbamate of physostigmine, is a reversible acetyl-selective cholinesterase inhibitor. In studies of rats with lesions of the forebrain cholinergic system, injections of phenserine was found to significantly decrease the levels of secreted beta-APP in the CSF of the rats. A study on cultured human brain cells found that phenserine reduces Abeta levels by regulating beta-APP translation.

MeSH：

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)

Absorption：

Rapidly absorbed and cleared from the body.

Biological Half-Life：

8 to 10 hours

Mechanism of Action：

Phenserine is a highly selective, reversible acetylcholinesterase inhibitor, a mechanism of action known to improve memory and cognition in Alzheimer’s subjects. Phenserine may prove to concentrate in the brain rapidly which would reduce the incidence of drug toxicity and side effects.

MeSH Entry Terms：

N-phenylcarbamoyl eseroline

Computed Properties

Molecular Weight:337.4
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:337.17902698
Monoisotopic Mass:337.17902698
Topological Polar Surface Area:44.8
Heavy Atom Count:25
Complexity:507
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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phenylserine CAS 101246-66-6

CAS No.: 101246-66-6

Grade: Pharmaceutical Grade

Content: 99%

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