Ramosetron hydrochloride

Iupac Name：(1-methylindol-3-yl)-[(5R)-4,5,6,7-tetrahydro-3H-benzimidazol-5-yl]methanone;hydrochloride

Molecular Weight：315.801

Modify Date.: 2022-11-01 06:08

Introduction: Nasea was launched in Japan for chemotherapy-induced emesis. Naseawas prepared by a four step sequence via the Vilsmeier-type coupling of 1-methylindole and 5-( 1- pyrrolidoncarbonyl)-4,5,6,7-tetrahydro-Hl -benzimidazolehydrochloride. The antiemetic activity arises because it is a potent 5-HT3 receptorantagonist that is i.v. and orally active. The (R)-isomer was found to be 100 timesmore potent than the (S)-isomer. It was able to inhibit cisplatin-induce emesis andwas 8670 times more potent than netoclopramide. View more+

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1. Names and Identifiers

1.1 Name: Ramosetron hydrochloride
1.2 Synonyms: (1-methyl-1h-indol-3-yl)(4,5,6,7-tetrahydro-1h-benzimidazol-5-yl)-methanon (1-Methyl-1H-indol-3-yl)[(5R)-4,5,6,7-tetrahydro-1H-benzimidazol-5-yl]methanone hydrochloride (1-Methyl-1H-indol-3-yl)[(5R)-4,5,6,7-tetrahydro-1H-benzimidazol-5-yl]methanone hydrochloride (1:1) (1-Methyl-1H-indol-3-yl)[(5R)-4,5,6,7-tetrahydro-1H-benzimidazol-5-yl]methanonhydrochlorid (1-methylindol-3-yl)-[(5r)-4,5,6,7-tetrahydro-3h-benzimidazol-5-yl]methanone hydrochloride (R)-(1-Methyl-1H-indol-3-yl)(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-6-yl)methanone hydrochloride (r)-5-((1-methyl-3-indolyl)carbonyl)-4,5,6,7-tetrahydro-1h-benzimidazolehydr (R)-5-[(1-Methyl-3-indolyl)carbonyl]-4,5,6,7-tetrahydro-1H-benzimidazole hydrochloride (r)-monohydrochlorid methanone, (1-methyl-1H-indol-3-yl)[(5R)-4,5,6,7-tetrahydro-1H-benzimidazol-5-yl]-, hydrochloride (1:1) Methanone, (1-methyl-1H-indol-3-yl)[(6R)-4,5,6,7-tetrahydro-1H-benzimidazol-6-yl]-, hydrochloride (1:1) Methanone,(1-Methyl-1H-indol-3-yl)[(6R)-4,5,6,7-tetrahydro-1H-benziMidazol-6-yl]-,hydrochloride (1:1) MFCD00894748 Nasea Ramosetron (Hydrochloride) RAMOSETRON HCL YM060

1.3 CAS No.: 132907-72-3

1.4 CID: 107999

1.5 Molecular Formula: C17H18ClN3O (isomer)

1.6 Inchi: InChI=1S/C17H17N3O.ClH/c1-20-9-13(12-4-2-3-5-16(12)20)17(21)11-6-7-14-15(8-11)19-10-18-14;/h2-5,9-11H,6-8H2,1H3,(H,18,19);1H/t11-;/m1./s1

1.7 InChkey: XIXYTCLDXQRHJO-RFVHGSKJSA-N

1.8 Canonical Smiles: CN1C=C(C2=CC=CC=C21)C(=O)C3CCC4=C(C3)NC=N4.Cl

1.9 Isomers Smiles: CN1C=C(C2=CC=CC=C21)C(=O)[C@@H]3CCC4=C(C3)NC=N4.Cl

2. Properties

2.1 Melting point: 244-246°C

2.1 Boiling point: 579.7°Cat760mmHg

2.1 Flash Point: 304.4°C

2.1 Precise Quality: 315.11400

2.1 PSA: 50.68000

2.1 logP: 3.69120

2.1 Solubility: H2O: soluble20mg/mL, clear

2.2 Appearance: white to beige

2.3 Storage: Hygroscopic, Refrigerator, Under Inert Atmosphere

2.4 Chemical Properties: White Solid

2.5 Color/Form: white to beige

2.6 Water Solubility: H2O: soluble20mg/mL, clear

2.7 StorageTemp: -20°C

3. Use and Manufacturing

3.1 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 24 companies from 1 notifications to the ECHA C&L Inventory.

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P270, P301+P312, P330, and P501

3.2 Usage: Selective serotonin 5HT3, receptor antagonist; structurally different from Ondansetron (O655000), Granisetron (G780000). Antiemetic.

4. Safety and Handling

4.1 Symbol: GHS07;

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: 22

4.1 Safety Statements: 22

4.1 Hazard Declaration: H302

4.1 RIDADR: NONH for all modes of transport

4.1 WGK Germany: 3

4.1 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD	intravenous	> 30mg/kg (30mg/kg)	SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE	Oyo Yakuri. Pharmacometrics. Vol. 47, Pg. 117, 1994.
dog	LD	oral	> 60mg/kg (60mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS GASTROINTESTINAL: NAUSEA OR VOMITING	Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 760, 1995.
mouse	LD50	intravenous	90mg/kg (90mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 27, Pg. 652, 1996.
rat	LD50	intravenous	151mg/kg (151mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Oyo Yakuri. Pharmacometrics. Vol. 47, Pg. 105, 1994.
rat	LD50	oral	1264mg/kg (1264mg/kg)	?	Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 41, Pg. 1048, 1999.

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

132907-72-3Total: 2 Synthesis Route

132036-39-6 15 Suppliers

132907-72-3 148 Suppliers

Literatures:
Chemical and Pharmaceutical Bulletin, , vol. 44, # 9 p. 1707 - 1716
Yield: null

132036-88-5 10 Suppliers

912850-42-1

912850-41-0

132907-72-3 148 Suppliers

Literatures:
WO2006/109762 A1, ; Page/Page column 10-11 ;
Yield: null

8. Precursor and Product

precursor:

132036-88-5

132036-39-6

9. Other Information

9.0 Chemical Properties: White Solid

9.1 Uses: Selective serotonin 5HT3, receptor antagonist; structurally different from Ondansetron (O655000), Granisetron (G780000). Antiemetic.

9.2 Target: Value

9.3 5-HT3 receptor (in N1E-15 cells): 0.091 nM(Ki)

9.4 Description: Nasea was launched in Japan for chemotherapy-induced emesis. Nasea was prepared by a four step sequence via the Vilsmeier-type coupling of 1- methylindole and 5-( 1- pyrrolidoncarbonyl)-4,5,6,7-tetrahydro-Hl -benzimidazole hydrochloride. The antiemetic activity arises because it is a potent 5-HT3 receptor antagonist that is i.v. and orally active. The (R)-isomer was found to be 100 times more potent than the (S)-isomer. It was able to inhibit cisplatin-induce emesis and was 8670 times more potent than netoclopramide.

9.5 Originator: Yamanouchi (Japan)

9.6 Brand name: Nasea

9.7 Biochem/physiol Actions: Ramosetron is a tetra hydrobenzimidazole derivative, containing an indole ring. It inhibits colon contraction mediated by serotonin, competitively.

10. Computational chemical data

Molecular Weight: 315.801g/mol
Molecular Formula: C₁₇H₁₈ClN₃O
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 315.1138399
Monoisotopic Mass: 315.1138399
Complexity: 413
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 50.7
Heavy Atom Count: 22
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB7IAAEAAAAAAAAAAAAAAAAAWLAAAAwYAAAAAAAAFgB/AAAHgAQAAAADQzBngQ/0PfNkACoA7R3ZACCgC21EqAJ2aE4dNiIaPrAnZGUIYhokALIyeccicCegAAAAAACAAAQAACAAAQAQAAAAAAAAA==

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