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Cevimeline

Cevimeline

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Also known as: 173553-37-2, 107220-28-0, Cevimeline hydrochloride, 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] (hydrochloride), Cevimeline hcl, 2-methylspiro[1,3-oxathiolane-5,3'-1-azabicyclo[2.2.2]octane];hydrochloride

Molecular Formula

C₁₀H₁₈ClNOS

Molecular Weight

235.77 g/mol

InChI Key

SURWTGAXEIEOGY-UHFFFAOYSA-N

Cevimeline Hydrochloride is a cholinergic analogue with glandular secretion stimulatory activity. Cevimeline binds to and activates muscarinic receptors, thereby increasing the secretions in exocrine salivary and sweat glands. This cholinergic agonist also increases the tone of smooth muscle in the gastrointestinal and urinary tracts. Cevimeline is being studied as a treatment for dry mouth caused by radiation therapy to the head and neck.

1 2D Structure

Cevimeline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-methylspiro[1,3-oxathiolane-5,3'-1-azabicyclo[2.2.2]octane];hydrochloride

2.1.2 InChI

InChI=1S/C10H17NOS.ClH/c1-8-12-10(7-13-8)6-11-4-2-9(10)3-5-11;/h8-9H,2-7H2,1H3;1H

2.1.3 InChI Key

SURWTGAXEIEOGY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1OC2(CN3CCC2CC3)CS1.Cl

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 2-methyspiro(1,3-oxathiolane-5,3)quinuclidine

2. Af 102b

3. Af 102b, (cis-(+))-isomer

4. Af 102b, (trans)-isomer

5. Af-102b

6. Af102b

7. Cevimeline

8. Cevimeline Hydrochloride

9. Evoxac

10. Fks 508

11. Fks-508

12. Sni 2011

13. Sni-2011

2.2.2 Depositor-Supplied Synonyms

1. 173553-37-2

2. 107220-28-0

3. Cevimeline Hydrochloride

4. 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] (hydrochloride)

5. Cevimeline Hcl

6. 2-methylspiro[1,3-oxathiolane-5,3'-1-azabicyclo[2.2.2]octane];hydrochloride

7. 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] Hydrochloride

8. Spiro[1-azabicyclo[2.2.2]octane-3,5'-[1,3]oxathiolane], 2'-methyl-,hydrochloride

9. Af-102b

10. Schembl861315

11. Dtxsid701338114

12. Bcp12519

13. Cs-b1634

14. Yga55337

15. Akos037650732

16. Cs-15234

17. Ft-0664491

18. A925456

19. J-001739

20. (+/-)-cis-2-methylspiro[1,3-oxathiolane-5,3'-quinuclidine]

21. Cis-2-methylspiro[1,3-oxathiolane-5,3'-quinuclidine]hydrochloride

22. 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] (hcl)

23. 5'-methyl-4-azaspiro[bicyclo[2.2.2]octane-2,2'-[1,4]oxathiolane] Hydrochloride

2.3 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₈ClNOS
Molecular Weight	235.77 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Exact Mass	235.0797631 g/mol
Monoisotopic Mass	235.0797631 g/mol
Topological Polar Surface Area	37.8 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	215
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Muscarinic Agonists

Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate. (See all compounds classified as Muscarinic Agonists.)

Parasympathomimetics

Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)

4.2 FDA Pharmacological Classification

4.2.1 Pharmacological Classes

Cholinergic Receptor Agonist [EPC]; Cholinergic Muscarinic Agonists [MoA]