CAS 153504-70-2|Cevimeline hydrochloride hemihydrate

Introduction：Basic information about CAS 153504-70-2|Cevimeline hydrochloride hemihydrate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Cevimeline hydrochloride hemihydrate BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles2
7. Synonyms

Common Name	Cevimeline hydrochloride hemihydrate
CAS Number	153504-70-2	Molecular Weight	435.09
Density	1.19g/cm3	Boiling Point	308.5ºC at 760mmHg
Molecular Formula	C₂₀H₃₅ClN₂O₂S₂	Melting Point	/
MSDS	USA	Flash Point	140.4ºC
Symbol	GHS06	Signal Word	Danger

Names

Name	Cevimelinehydrochloride
Synonym	More Synonyms

Cevimeline hydrochloride hemihydrate BiologicalActivity

Description	Cevimeline hydrochloride hemihydrate, a novel muscarinic receptor agonist, is a candidate therapeutic drug for xerostomia in Sjogren's syndrome. IC50 value:Target: mAChRThe general pharmacol. properties of this drug on the gastrointestinal, urinary, and reproductive systems and other tissues were investigated in mice, rats, guinea pigs, rabbits, and dogs. The in vitro metab. of SNI-2011 was also evaluated with rat and dog liver microsomes. After oral administration, plasma concns. of SNI-2011 reached to Cmax within 1 h in both species, suggesting that SNI-2011 was quickly absorbed, and then decreased with a t1/2 of 0.4-1.1 h. The bioavailability was 50% and 30% in rats and dogs, resp. Major metabolites in plasma were both S- and N-oxidized metabolites in rats and only N-oxidized metabolite in dogs, indicating that a large species difference was obsd. in the metab. of SNI-2011. Sex difference was also obsd. in the pharmacokinetics of SNI-2011 in rats, but not in dogs. In the in vitro study, chem. inhibition and pH-dependent studies revealed that the sulfoxidn. and N-oxidn. of SNI-2011 were mediated by cytochrome P 450 (CYP) and flavin-contg. monooxygenase (FMO), resp., in both species. In addn., CYP2D and CYP3A were mainly responsible for the sulfoxidn. in rat liver microsomes.
Related Catalog	Signaling Pathways >>GPCR/G Protein >>mAChRSignaling Pathways >>Neuronal Signaling >>mAChRResearch Areas >>Neurological Disease
References	[1]. Iga Y, Arisawa H, Ogane N, Saito Y, Tomizuka T, Nakagawa-Yagi Y, Masunaga H, Yasuda H, Miyata N. (+/-)-cis-2-methylspiro[1,3-oxathiolane-5,3'-quinuclidine] hydrochloride, hemihydrate (SNI-2011, cevimeline hydrochloride) induces saliva and tear secretions [2]. Omori Y, Asari T, Maruyama K, Kusama H, Kojima M, Shibata N. Effects of pilocarpine hydrochloride and cevimeline on submandibular/sublingual salivation in rat xerostomia model produced by X-ray irradiation. Arzneimittelforschung. 2003;53(5):342-50. [3]. Washio, Takuo; Kohsaka, Kazuhiro; Arisawa, Hirohiko; et al.Pharmacokinetics and metabolism of radiolabeled SNI-2011, a novel muscarinic receptor agonist, in healthy volunteers: Comprehensive understanding of absorption, metabolism and excretion using radi [4]. Washio, Takuo; Kohsaka, Kazuhiro; Arisawa, Hirohiko; et al.Pharmacokinetics and metabolism of the novel muscarinic receptor agonist SNI-2011 in rats and dogs.Arzneimittel-Forschung (2003), 53(1), 26-33. [5]. Arisawa, Hirohiko; Fukui, Kenji; Imai, Eiichi; et al.General pharmacological profile of the novel muscarinic receptor agonist SNI-2011, a drug for xerostomia in Sjogren's syndrome. Arzneimittel-Forschung (2002), 52(4), 225-232.

Description

Cevimeline hydrochloride hemihydrate, a novel muscarinic receptor agonist, is a candidate therapeutic drug for xerostomia in Sjogren's syndrome. IC50 value:Target: mAChRThe general pharmacol. properties of this drug on the gastrointestinal, urinary, and reproductive systems and other tissues were investigated in mice, rats, guinea pigs, rabbits, and dogs. The in vitro metab. of SNI-2011 was also evaluated with rat and dog liver microsomes. After oral administration, plasma concns. of SNI-2011 reached to Cmax within 1 h in both species, suggesting that SNI-2011 was quickly absorbed, and then decreased with a t1/2 of 0.4-1.1 h. The bioavailability was 50% and 30% in rats and dogs, resp. Major metabolites in plasma were both S- and N-oxidized metabolites in rats and only N-oxidized metabolite in dogs, indicating that a large species difference was obsd. in the metab. of SNI-2011. Sex difference was also obsd. in the pharmacokinetics of SNI-2011 in rats, but not in dogs. In the in vitro study, chem. inhibition and pH-dependent studies revealed that the sulfoxidn. and N-oxidn. of SNI-2011 were mediated by cytochrome P 450 (CYP) and flavin-contg. monooxygenase (FMO), resp., in both species. In addn., CYP2D and CYP3A were mainly responsible for the sulfoxidn. in rat liver microsomes.

Related Catalog

Signaling Pathways >>GPCR/G Protein >>mAChRSignaling Pathways >>Neuronal Signaling >>mAChRResearch Areas >>Neurological Disease

References

[1]. Iga Y, Arisawa H, Ogane N, Saito Y, Tomizuka T, Nakagawa-Yagi Y, Masunaga H, Yasuda H, Miyata N. (+/-)-cis-2-methylspiro[1,3-oxathiolane-5,3'-quinuclidine] hydrochloride, hemihydrate (SNI-2011, cevimeline hydrochloride) induces saliva and tear secretions

[2]. Omori Y, Asari T, Maruyama K, Kusama H, Kojima M, Shibata N. Effects of pilocarpine hydrochloride and cevimeline on submandibular/sublingual salivation in rat xerostomia model produced by X-ray irradiation. Arzneimittelforschung. 2003;53(5):342-50.

[3]. Washio, Takuo; Kohsaka, Kazuhiro; Arisawa, Hirohiko; et al.Pharmacokinetics and metabolism of radiolabeled SNI-2011, a novel muscarinic receptor agonist, in healthy volunteers: Comprehensive understanding of absorption, metabolism and excretion using radi

[4]. Washio, Takuo; Kohsaka, Kazuhiro; Arisawa, Hirohiko; et al.Pharmacokinetics and metabolism of the novel muscarinic receptor agonist SNI-2011 in rats and dogs.Arzneimittel-Forschung (2003), 53(1), 26-33.

[5]. Arisawa, Hirohiko; Fukui, Kenji; Imai, Eiichi; et al.General pharmacological profile of the novel muscarinic receptor agonist SNI-2011, a drug for xerostomia in Sjogren's syndrome. Arzneimittel-Forschung (2002), 52(4), 225-232.

Chemical & Physical Properties

Density	1.19g/cm3
Boiling Point	308.5ºC at 760mmHg
Molecular Formula	C₂₀H₃₅ClN₂O₂S₂
Molecular Weight	435.09
Flash Point	140.4ºC
PSA	84.77000
LogP	4.53590
Vapour Pressure	0.000676mmHg at 25°C
InChIKey	ZSTLCHCDLIUXJE-GMLJRNIPSA-N
SMILES	CC1OC2(CS1)CN1CCC2CC1.CC1OC2(CS1)CN1CCC2CC1.Cl.Cl.O
Storage condition	-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WG9634812

CAS REGISTRY NUMBER :: 153504-70-2

LAST UPDATED :: 199703

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C10-H17-N-O-S.Cl-H.1/2H2-O

MOLECULAR WEIGHT :: 244.78

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 139 mg/kg

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

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5340821

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 65 mg/kg

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

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5340821

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 40800 ug/kg

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

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5340821

Safety Information

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301
Precautionary Statements	P301 + P310
RIDADR	UN 2811 6.1 / PGIII

Articles2

Effects of pilocarpine and cevimeline on Ca2+ mobilization in rat parotid acini and ducts.

J. Med. Invest. 56 Suppl , 375, (2009)

Previous reports suggested that there is no significant difference in the binding affinity of pilocarpine and cevimeline on muscarinic receptors (1). However, in vivo studies from our laboratory sugge...

Cevimeline enhances the excitability of rat superior salivatory neurons.

J. Med. Invest. 56 Suppl , 267-9, (2009)

Cevimeline, a therapeutic drug for xerostomia, is an agonist of muscarinic acetylcholine receptors (mAChRs), and directly stimulates the peripheral mAChRs of the salivary glands. Since cevimeline is d...

Synonyms

Spiro[1-azabicyclo[2.2.2]octane-3,5'-[1,3]oxathiolane], 2'-methyl-, (3R)-, hydrochloride, hydrate (2:2:1)

cis-2-Methylspiro(1,3-oxathiolane-5,3')quinuclidine hydrochloride hydrate (2:2:1)

Unii-p81Q6V85np

(+/-)-cis-2-Methylspiro[1,3-oxathiolane-5,3'-quinuclidine] hydrochloride hemihydrate

cevimeline hydrochloride

(2R,2'R)-2'-Methylspiro[4-azabicyclo[2.2.2]octane-2,5'-[1,3]oxathiolane] hydrochloride hydrate (2:2:1)

CeviMeline hydrochloride heMihydrates

Cevimeline hydrochloride hemihydrate

(2R)-2'-Methylspiro[4-azabicyclo[2.2.2]octane-2,5'-[1,3]oxathiolane] hydrochloride hydrate (2:2:1)

Spiro[1-azabicyclo[2.2.2]octane-3,5'-[1,3]oxathiolane], 2'-methyl-, (2'R,3R)-, hydrochloride, hydrate (2:2:1)

(+/-)-cis-2-methylspiro[1,2-oxathiolane-5,3'-quinclidine] monohydrochloride

Cevimeline HCl 1/2H2o

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

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

CevimelineHCl

Cevimeline (hydrochloride hemihydrate)

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