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22260-51-1

22260-51-1 structure
22260-51-1 structure
  • Name: CB-154 mesylate
  • Chemical Name: bromocriptine methanesulfonate
  • CAS Number: 22260-51-1
  • Molecular Formula: C33H44BrN5O8S
  • Molecular Weight: 750.700
  • Catalog: API Nervous system medication Anti-shock palsy
  • Create Date: 2018-06-16 09:36:36
  • Modify Date: 2024-01-02 10:41:57
  • Bromocriptine mesylate is a potent dopamine D2/D3 receptor agonist, which binds D2 dopamine receptor with pKi of 8.05±0.2.

Name bromocriptine methanesulfonate
Synonyms (5'α)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-3',6',18-trioxoergotaman methanesulfonate (salt)
Bromocriptine mesilate
(6aR,9R)-5-bromo-N-[(2R,5S,10aS,10bS)-10b-hydroxy-2-(1-methylethyl)-5-(2-methylpropyl)-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide methanesulfonate (salt)
CB-154 mesylate
acide méthanesulfonique - (6aR,9R)-5-bromo-N-[(2R,5S,10aS,10bS)-10b-hydroxy-2-(1-méthyléthyl)-5-(2-méthylpropyl)-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-méthyl-4,6,6a,7,
Apo-Bromocriptine
2-Bromine-a-ergocryptine Methanesulfonate
Parlodel
2-Bromo α-Ergocryptine Mesylate
(5'α)-2-bromo-12'-hydroxy-5'-(2-methylpropyl)-3',6',18-trioxo-2'-(propan-2-yl)ergotaman methanesulfonate (1:1)
hydroindolo[4,3-fg]chinolin-9-carboxamid(1:1)
acide méthanesulfonique - (6aR,9R)-5-bromo-N-[(2R,5S,10aS,10bS)-10b-hydroxy-2-(1-méthyléthyl)-5-(2-méthylpropyl)-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-méthyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoléine-9-carboxamide (1:1)
Methansulfonsäure--(6aR,9R)-5-brom-N-[(2R,5S,10aS,10bS)-10b-hydroxy-2-(1-methylethyl)-5-(2-methylpropyl)-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]chinolin-9-carboxamid(1:1)
EINECS 244-881-1
2-Bromo-12'-hydroxy-5'a-isobutyl-2'-isopropylergotaman-3',6',18-trione Monomethanesulphonate
(5'α)-2-Bromo-12'-hydroxy-5'-isobutyl-2'-isopropyl-3',6',18-trioxoergotaman methanesulfonate (1:1)
Ergotaman, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-3',6',18-trioxo-, (5'α)-, methanesulfonate (1:1) (salt)
(6aR,9R)-5-bromo-N-[(2R,5S,10aS,10bS)-10b-hydroxy-2-(1-methylethyl)-5-(2-methylpropyl)-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg
Methansulfonsäure--(6aR,9R)-5-brom-N-[(2R,5S,10aS,10bS)-10b-hydroxy-2-(1-methylethyl)-5-(2-methylpropyl)-3,6-dioxooctahydro-8H-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9-hexa
MFCD00069218
8,9-hexahydroindolo[4,3-fg]quinoléine-9-carboxamide (1:1)
Bromocriptine (mesylate)
Description Bromocriptine mesylate is a potent dopamine D2/D3 receptor agonist, which binds D2 dopamine receptor with pKi of 8.05±0.2.
Related Catalog
Target

pKi: 8.05±0.2 (dopamine D2 receptor)[1]

In Vitro Bromocriptine stimulates [35S]-GTPγS binding at D2 dopamine receptor expressed in CHO cells with pEC50 of 8.15±0.05[1]. Bromocriptine also is a strong inhibitor of brain nitric oxide synthase. The ergot alkaloid Bromocriptine (BKT) is found to act as a strong inhibitor of purified neuronal nitric oxide synthase (NOS) (IC50=10±2 μM) whereas it is poorly active towards inducible macrophage NOS (IC50>100 μM) [2]. Bromocriptine is found to inhibit the activity of at least one human cytochrome P450 enzyme. Bromocriptine is a potent inhibitor of CYP3A4 with a calculated IC50 value for the interaction of 1.69 μM[3].
In Vivo Bromocriptine mesylate (2 mg/kg, i.p.) is administered for 7 days in groups of mice in forced swimming test (FST) and tail suspension test (TST). Bromocriptine group shows significant anti-immobility action as compared to control. When Bromocriptine administered 30 min after the last dose of 7 days MPE treatment and subjected to FST, this dopaminergic agonist produces significant and dose dependent potentiation of anti-immobility action of MPE (200 mg/kg, p.o.) as compared to MPE treatment alone. Bromocriptine treatment group shows a significant reduction of immobility time as compared to control. Bromocriptine administration after 7 days pretreatment with MPE (100 and 200 mg/kg, p.o.) shows significant and dose dependent potentiation of anti-immobility action of MPE as compared to MPE treatment alone[4]. Intracisternal administration of Bromocriptine decreases significantly the static mechanical allodynia (SMA) score compared to that of sham (saline-injected rats) and its effect lasted for 30 min. Intraperitoneal administration of Bromocriptine induces a significant, dose dependent (0.1 mg and 1 mg/kg) decrease in pain scores in CCI-IoN group when compared to sham and its effect lasted for 6 h. The highest dose induces the highest score decrease (P<0.01). Bromocriptine effect lasts for 20 min. Intraperitoneal administration of Bromocriptine induces a significant dose dependent decrease in SMA score in CCI-IoN+6-OHDA lesioned group compared to that of sham. Its effect lasts for 6 h[5].
Kinase Assay The [35S]-GTPγS binding assay is carried out. Cell membranes (25 ±75 ug) are incubated in Buffer B containing 0.1 mM dithiothreitol (DTT) and 1 uM GDP and drugs in a volume of 0.9 mL for 30 min at 30°C. This preincubation ensures that the agonists tested are at equilibrium when the [35S]-GTPγS (50±150 pM, final concentration) is added (in 100 uL ofBuffer B) to initiate the reaction. The assay mixture is incubated for a further 20 min unless otherwise stated. The assays are terminated by rapid filtration and bound radio-activity determined as described for the radio-ligand binding assays above. The total binding of [35S]-GTPγS is less than 20% of that added[1].
Animal Admin Mice[4] Swiss mice (20-25 g) of either sex (total 150) are used. Bromocriptine mesylate is used as dopamine receptor (D2) agonist. Haloperidol is diluted in distilled water which is used for a vehicle of injection. Bromocriptine mesylate is dissolved in one drop of glacial acetic acid and made up to volume in distilled water. Imipramine is dissolved in 0.9% normal saline. Haloperidol (0.1 mg/kg, i.p.) and Bromocriptine mesylate (2 mg/kg, i.p.) are administered for 7 days in groups of mice in Forced Swimming Test (FST) and Tail Suspension Test (TST). Imipramine (10 mg/kg, p.o.) as a standard is administered in positive control groups for 7 days. Rats[5] Adult male Sprague-Dawley rats (N=112, 275-325 g) are used. Two weeks after the 6-OHDA injection, the animals are briefly (<3 min) anesthetized with 2 % halothane using a mask and received for intracisternal administration Bromocriptine (7 μg/kg dissolved in 5 μL vehicle) or the vehicle alone (5 μL of 0.9 % saline). For i.p. injection we used Bromocriptine (1 mg/kg) and SKF81297 (3 mg/kg dissolved in 0.9 % saline) concentrations. Following a recovery period (<2 min), the rats are placed in the observation field for 40 min period-test by a blind-experimenter.
References

[1]. Gardner B, et al. Agonist action at D2(long) dopamine receptors: ligand binding and functional assays. Br J Pharmacol. 1998 Jul;124(5):978-84.

[2]. Renodon A, et al. Bromocriptine is a strong inhibitor of brain nitric oxide synthase: possible consequences for the origin of its therapeutic effects.FEBS Lett. 1997 Apr 7;406(1-2):33-6.

[3]. Wynalda MA, et al. Assessment of potential interactions between dopamine receptor agonists and various human cytochrome P450 enzymes using a simple in vitro inhibition screen. Drug Metab Dispos. 1997 Oct;25(10):1211-4.

[4]. Rana DG, et al. Dopamine mediated antidepressant effect of Mucuna pruriens seeds in various experimental models of depression. Ayu. 2014 Jan;35(1):90-7.

[5]. Dieb W, et al. Nigrostriatal dopaminergic depletion increases static orofacial allodynia. J Headache Pain. 2016;17:11.

Boiling Point 891.3ºC at 760 mmHg
Molecular Formula C33H44BrN5O8S
Molecular Weight 750.700
Flash Point 492.8ºC
Exact Mass 749.209412
PSA 180.96000
LogP 3.98220
Vapour Pressure 0mmHg at 25°C
Water Solubility H2O: 0.8 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KE1595000
CHEMICAL NAME :
alpha-Ergocryptine, 2-bromo-, methanesulfonate
CAS REGISTRY NUMBER :
22260-51-1
LAST UPDATED :
199504
DATA ITEMS CITED :
24
MOLECULAR FORMULA :
C32-H4O-Br-N5-O5.C-H4-O3-S
MOLECULAR WEIGHT :
714.43

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
50 ug/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 340,1410,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
650 ug/kg/9D-I
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions Behavioral - headache Cardiac - cardiomyopathy including infarction
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 118,199,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
375 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Cardiac - pulse rate increase, without fall in BP Lungs, Thorax, or Respiration - respiratory stimulation
REFERENCE :
JOPDAB Journal of Pediatrics. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) V.1- 1932- Volume(issue)/page/year: 105,838,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1 mg/kg/20D-I
TOXIC EFFECTS :
Behavioral - toxic psychosis
REFERENCE :
AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 143,935,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
52 mg/kg/35W-I
TOXIC EFFECTS :
Brain and Coverings - changes in cerebral spinal fluid
REFERENCE :
NEURAI Neurology. (Modern Medicine Pub., Inc., 1 E. First St., Duluth, MN 55802) V.1- 1951- Volume(issue)/page/year: 35,1193,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 30,809,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 30,809,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 29,1231,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2502 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 30,809,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
189 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 30,809,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 30,809,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
8200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,232,1979 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1400 mg/kg
SEX/DURATION :
lactating female 1-14 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Maternal Effects - postpartum
REFERENCE :
JRPMAP Journal of Reproductive Medicine. (2 Jacklynn Ct., St. Louis, MO 63132) V.3- 1969- Volume(issue)/page/year: 33,630,1988
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
42 mg/kg
SEX/DURATION :
female 1-7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 30,1358,1974
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
60 mg/kg
SEX/DURATION :
female 6 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - other effects
REFERENCE :
BIREBV Biology of Reproduction. (Soc. for the Study of Reproduction, 309 W. Clark St., Champaign, IL 61820) V.1- 1969- Volume(issue)/page/year: 34,788,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
3 mg/kg
SEX/DURATION :
male 15 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
IJANDP International Journal of Andrology. (Scriptor Publisher ApS, 15 Gasvaerksvej, DK-1656 Copenhagen V, Denmark) V.1- 1978- Volume(issue)/page/year: 5,331,1982
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
10500 ug/kg
SEX/DURATION :
female 1-7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 30,1358,1974
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
225 ug/kg
SEX/DURATION :
female 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 24,1130,1968
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
10500 ug/kg
SEX/DURATION :
female 6-8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - postpartum
REFERENCE :
EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 24,1130,1968
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
2 mg/kg
SEX/DURATION :
female 5 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
REFERENCE :
TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 50,189,1990
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
35 mg/kg
SEX/DURATION :
female 14-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - other effects to embryo
REFERENCE :
GCENA5 General and Comparative Endocrinology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1961- Volume(issue)/page/year: 39,118,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
20 mg/kg
SEX/DURATION :
male 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Paternal Effects - other effects on male
REFERENCE :
IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 23,679,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
3 mg/kg
SEX/DURATION :
lactating female 3 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Maternal Effects - postpartum
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,51,1976 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4920 No. of Facilities: 27 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 499 (estimated) No. of Female Employees: 225 (estimated)
Symbol GHS07 GHS09
GHS07, GHS09
Signal Word Warning
Hazard Statements H302-H410
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn: Harmful;
Risk Phrases R20/21/22
Safety Phrases S22-S24/25
RIDADR UN 3077 9 / PGIII
WGK Germany 3
RTECS KE1595000