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Posiphen

Synopsis, Chemistry

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Also known as: (+)-phenserine, R-phenserine, 116839-68-0, (+)-posiphen, Phenserine, (+)-, Buntanetap

Molecular Formula

C₂₀H₂₃N₃O₂

Molecular Weight

337.4 g/mol

InChI Key

PBHFNBQPZCRWQP-AZUAARDMSA-N

FDA UNII

Z0O4TJ588O

Posiphen is under investigation in clinical trial NCT02925650 (Safety, Tolerability, PK and PD of Posiphen in Subjects With Early Alzheimer's Disease).

1 2D Structure

(+)-Posiphen

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(3aS,8bR)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-phenylcarbamate

2.1.2 InChI

InChI=1S/C20H23N3O2/c1-20-11-12-22(2)18(20)23(3)17-10-9-15(13-16(17)20)25-19(24)21-14-7-5-4-6-8-14/h4-10,13,18H,11-12H2,1-3H3,(H,21,24)/t18-,20+/m0/s1

2.1.3 InChI Key

PBHFNBQPZCRWQP-AZUAARDMSA-N

2.1.4 Canonical SMILES

CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC4=CC=CC=C4)C)C

2.1.5 Isomeric SMILES

C[C@]12CCN([C@H]1N(C3=C2C=C(C=C3)OC(=O)NC4=CC=CC=C4)C)C

2.2 Other Identifiers

2.2.1 UNII

Z0O4TJ588O

2.3 Synonyms

2.3.1 MeSH Synonyms

1. N-phenylcarbamoyl Eseroline

2. N-phenylcarbamoyleseroline

3. Phenserine

2.3.2 Depositor-Supplied Synonyms

1. (+)-phenserine

2. R-phenserine

3. 116839-68-0

4. (+)-posiphen

5. Phenserine, (+)-

6. Buntanetap

7. Anvs401

8. Buntanetap [usan]

9. (+)-phenylcarbamoyleseroline

10. Anvs-401

11. Z0o4tj588o

12. (+)-o-(phenylcarbamoyl)eseroline

13. (3ar,8as)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl Phenylcarbamate

14. Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(n-phenylcarbamate), (3ar,8as)-

15. Unii-z0o4tj588o

16. Chembl4297417

17. Dtxsid001110145

18. Who 12342

19. Db15317

20. Hy-16009

21. Cs-0006062

22. [(3as,8br)-3,4,8b-trimethyl-2,3a-dihydro-1h-pyrrolo[2,3-b]indol-7-yl] N-phenylcarbamate

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₃N₃O₂
Molecular Weight	337.4 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	337.17902698 g/mol
Monoisotopic Mass	337.17902698 g/mol
Topological Polar Surface Area	44.8 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	507
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Cholinesterase Inhibitors

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.)