CAS 91374-20-8|Ropinirole hydrochloride

Introduction：Basic information about CAS 91374-20-8|Ropinirole hydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Ropinirole hydrochloride BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles27
8. Synonyms

Common Name	Ropinirole hydrochloride
CAS Number	91374-20-8	Molecular Weight	296.836
Density	/	Boiling Point	410.5ºC at 760mmHg
Molecular Formula	C₁₆H₂₅ClN₂O	Melting Point	241-243ºC
MSDS	ChineseUSA	Flash Point	/
Symbol	GHS07, GHS09	Signal Word	Warning

Names

Name	4-(2-(Dipropylamino)ethyl)indolin-2-one hydrochloride
Synonym	More Synonyms

Ropinirole hydrochloride BiologicalActivity

Description	Ropinirole hydrochloride(SKF101468 hydrochloride) a selective dopamine D2 receptor inhibitor with IC50 of 29 nM.Target: Dopamine D2 ReceptorRopinirole (50 mg/kg, i.p.) causes biphasic spontaneous locomotor activity in mice. Ropinirole (0.05-1.0 mg/kg SC) dose-dependently inhibits the dyskinesias induced by 2-di-n-propylamino-5,6-di-hydroxytetralin in mice. Ropirtirole, at doses of 1 and 10 μg, injected unilaterally directly into the striatum of the rat causes marked, contralateral (away from the side of injection) asymmetry and circling in mice. Ropinirole (0.05-1.0 mg/kg SC or 0.1 mg/kg PO) reverses all motor and behavioural deficits induced by MPTP in marmosets [1]. Ropinirole (2 mg/kg, i.p.) for 7 days increases GSH, catalase and SOD activities in the striatum and protected striatal dopaminergic neurons against 6-hydroxydopamine (6-OHDA) in mice [2]. Ropinirole (0.2 mg/kg, i.p.) improves the use of previously akinetic forelimb and produced robust circling behavior in lesioned rats with striatal over-expression of both D2R and D3R compared to lesioned animals that received blank vector. The subtherapeutic dose of ropinirole generates only modest motor effects in lesioned rats with sole over-expression of D2R or D3R [3]. Ropinirole (1-8 mg t.i.d.) is rapidly and completely absorbed with oral bioavailability of 55%, clearance of 780 mL/min, elimination half-life of 6 hours in healthy volunteer. Since the major route of elimination for Ropinirole is by the CYP enzyme system, mainly by CYP1A2 and also by CYP3A4, inhibition of the former and possibly the latter may reduce the agent's clearance and lead to drug accumulation [4].
Related Catalog	Signaling Pathways >>GPCR/G Protein >>Dopamine ReceptorSignaling Pathways >>Neuronal Signaling >>Dopamine ReceptorResearch Areas >>Neurological Disease
References	[1]. Eden, R.J., et al., Preclinical pharmacology of ropinirole (SK&F 101468-A) a novel dopamine D2 agonist. Pharmacol Biochem Behav, 1991. 38(1): p. 147-54. [2]. Iida, M., et al., Dopamine D2 receptor-mediated antioxidant and neuroprotective effects of ropinirole, a dopamine agonist. Brain Res, 1999. 838(1-2): p. 51-9. [3]. Lam, Y.W., Clinical pharmacology of dopamine agonists. Pharmacotherapy, 2000. 20(1 Pt 2): p. 17S-25S. [4]. Allen, R., et al., Ropinirole decreases periodic leg movements and improves sleep parameters in patients with restless legs syndrome. Sleep, 2004. 27(5): p. 907-14.

Description

Ropinirole hydrochloride(SKF101468 hydrochloride) a selective dopamine D2 receptor inhibitor with IC50 of 29 nM.Target: Dopamine D2 ReceptorRopinirole (50 mg/kg, i.p.) causes biphasic spontaneous locomotor activity in mice. Ropinirole (0.05-1.0 mg/kg SC) dose-dependently inhibits the dyskinesias induced by 2-di-n-propylamino-5,6-di-hydroxytetralin in mice. Ropirtirole, at doses of 1 and 10 μg, injected unilaterally directly into the striatum of the rat causes marked, contralateral (away from the side of injection) asymmetry and circling in mice. Ropinirole (0.05-1.0 mg/kg SC or 0.1 mg/kg PO) reverses all motor and behavioural deficits induced by MPTP in marmosets [1]. Ropinirole (2 mg/kg, i.p.) for 7 days increases GSH, catalase and SOD activities in the striatum and protected striatal dopaminergic neurons against 6-hydroxydopamine (6-OHDA) in mice [2]. Ropinirole (0.2 mg/kg, i.p.) improves the use of previously akinetic forelimb and produced robust circling behavior in lesioned rats with striatal over-expression of both D2R and D3R compared to lesioned animals that received blank vector. The subtherapeutic dose of ropinirole generates only modest motor effects in lesioned rats with sole over-expression of D2R or D3R [3]. Ropinirole (1-8 mg t.i.d.) is rapidly and completely absorbed with oral bioavailability of 55%, clearance of 780 mL/min, elimination half-life of 6 hours in healthy volunteer. Since the major route of elimination for Ropinirole is by the CYP enzyme system, mainly by CYP1A2 and also by CYP3A4, inhibition of the former and possibly the latter may reduce the agent's clearance and lead to drug accumulation [4].

Related Catalog

Signaling Pathways >>GPCR/G Protein >>Dopamine ReceptorSignaling Pathways >>Neuronal Signaling >>Dopamine ReceptorResearch Areas >>Neurological Disease

References

[1]. Eden, R.J., et al., Preclinical pharmacology of ropinirole (SK&F 101468-A) a novel dopamine D2 agonist. Pharmacol Biochem Behav, 1991. 38(1): p. 147-54.

[2]. Iida, M., et al., Dopamine D2 receptor-mediated antioxidant and neuroprotective effects of ropinirole, a dopamine agonist. Brain Res, 1999. 838(1-2): p. 51-9.

[3]. Lam, Y.W., Clinical pharmacology of dopamine agonists. Pharmacotherapy, 2000. 20(1 Pt 2): p. 17S-25S.

[4]. Allen, R., et al., Ropinirole decreases periodic leg movements and improves sleep parameters in patients with restless legs syndrome. Sleep, 2004. 27(5): p. 907-14.

Chemical & Physical Properties

Boiling Point	410.5ºC at 760mmHg
Melting Point	241-243ºC
Molecular Formula	C₁₆H₂₅ClN₂O
Molecular Weight	296.836
Exact Mass	296.165527
PSA	32.34000
LogP	3.78570
InChIKey	XDXHAEQXIBQUEZ-UHFFFAOYSA-N
SMILES	CCCN(CCC)CCc1cccc2c1CC(=O)N2.Cl
Storage condition	Room temp

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM3288250

CHEMICAL NAME :: 2H-Indol-2-one, 1,3-dihydro-4-(2-(dipropylamino)ethyl)-, monohydrochloride

CAS REGISTRY NUMBER :: 91374-20-8

LAST UPDATED :: 199807

DATA ITEMS CITED :: 9

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 396 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 11),S1725,199

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 71 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 11),S1725,199 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1500 mg/kg/30D-I

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - changes in adrenal weight Related to Chronic Data - changes in ovarian weight

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 11),S1731,199

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 18250 mg/kg/1Y-I

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Kidney, Ureter, Bladder - other changes Endocrine - changes in adrenal weight

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 11),S1731,199

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 450 mg/kg/30D-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - excitement Skin and Appendages - hair

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 11),S1741,199

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 5475 mg/kg/1Y-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - changes in ovarian weight Related to Chronic Data - changes in testicular weight

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 11),S1741,199 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3040 mg/kg

SEX/DURATION :: female 2 week(s) pre-mating - 20 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 11),S1747,199

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 11),S1747,199

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 280 mg/kg

SEX/DURATION :: female 15-21 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 11),S1747,199

Safety Information

Symbol	GHS07, GHS09
Signal Word	Warning
Hazard Statements	H302-H400
Precautionary Statements	P301 + P312 + P330
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes	Xn,N
Risk Phrases	R22
Safety Phrases	36-60-61-37/39-26
RIDADR	UN 3077 9/PG 3
RTECS	NM3288250
Hazard Class	9.0
HS Code	2933790090

Customs

HS Code	2933790090
Summary	2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%

Articles27

Sustained release microspheres of ropinirole hydrochloride: effect of process parameters.

Acta. Pharm. 61 , 363-376, (2011)

An emulsion solvent evaporation method was employed to prepare microspheres of ropinirole hydrochloride, a highly water soluble drug, by using ethylcellulose and PEG with the help of 32 full factorial...

Serotonergic and dopaminergic mechanisms in graft-induced dyskinesia in a rat model of Parkinson's disease

Neurobiol. Dis. 47(3) , 393-406, (2012)

Dyskinesia seen in the off-state, referred as graft-induced dyskinesia (GID), has emerged as a serious complication induced by dopamine (DA) cell transplantation in parkinsonian patients. Although the...

Structure-activity relationship study of N⁶-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine analogues: development of highly selective D3 dopamine receptor agonists along with a highly potent D2/D3 agonist and their pharmacological characterization.

J. Med. Chem. 55(12) , 5826-40, (2012)

In our effort to develop multifunctional drugs against Parkinson's disease, a structure-activity-relationship study was carried out based on our hybrid molecular template targeting D2/D3 receptors. Co...

Synonyms

2H-Indol-2-one, 4-[2-(dipropylamino)ethyl]-1,3-dihydro-, hydrochloride (1:1)

4-[2-(Dipropylamino)ethyl]-1,3-dihydro-2H-indol-2-one hydrochloride

4-[2-(Dipropylamino)ethyl]-1,3-dihydro-2H-indol-2-one hydrochloride (1:1)

4-[2-(Dipropylamino)ethyl]-1,3-dihydro-2H-indol-2-onhydrochlorid

UNII-D7ZD41RZI9

ropinirole hcl

4-[2-(dipropylamino)éthyl]-1,3-dihydro-2H-indol-2-one chlorhydrate

Adartrel

MFCD01754173

Ropinirole hydrochloride

2H-indol-2-one, 4-[2-(dipropylamino)ethyl]-1,3-dihydro-, monohydrochloride

Requip

Ropinirole (hydrochloride)

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