155206-00-1 Usage
Description
Bimatoprost, also known as Lumigan, is a synthetic prostamide that is structurally related to prostaglandin F2α. It is a crystalline solid and is supplied as a sterile 0.03% ophthalmic solution. Bimatoprost is used to reduce elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension, which is a proven risk of glaucomatous visual field loss. It exhibits a unique pharmacological profile by contracting the feline iris sphincter without interacting with any known prostanoid receptors. Bimatoprost mimics the action of endogenous prostamides on specific receptors that lower IOP by increasing aqueous humor outflow through both pressure-insensitive and pressure-sensitive pathways without reducing humor formation.
Uses
Used in Ophthalmology:
Bimatoprost is used as an antiglaucoma agent for the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension. It is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. Bimatoprost reduces intraocular pressure by increasing the outflow of aqueous fluid from the eyes.
Used in Pharmaceutical Industry:
Bimatoprost is used as an ocular hypotensive drug, specifically as a prostaglandin F2α analog. It has been approved for use in the pharmaceutical industry due to its effectiveness in reducing IOP and its good tolerance and systemic safety profile compared to other medications like latanoprost. Bimatoprost is prepared by esterification of 17-phenyl-18,19,20-trinorprostaglandin F2α followed by ethylamidation.
Brand Name:
Lumigan (Allergan) is the brand name under which Bimatoprost is marketed. The recommended dosage of bimatoprost is limited to one drop into the affected eye once daily in the evening. Increased usage may decrease its beneficial effect. If used concurrently with other IOP-lowering drugs, a waiting period of 5 minutes should separate administrations.
Glaucoma Drug
Bimatoprost is a synthetic amide F2α derivative ,it can selectively simulate the effect forefront amines produced by the body, which make aqueous humor production rate increase aqueous outflow resistance is reduced, by increasing the amount of aqueous outflow of the uveoscleral and trabecular Netcom channel to reduce intraocular pressure (IOP),it is considered to be the most effective hypotensive drug of topical ocular anti-glaucoma drugs,it is suitable for the treatment of open-angle glaucoma (POAG) or invalid elevated intraocular other ocular hypotensive medications compression syndrome (OHT) patients.
Side effects
1. to deepen the color of the iris, blepharitis, eye irritation and pain; black eyelashes thicker growth; conjunctival hyperemia, temporarily punctate corneal epithelial erosion, eyelid edema and erythema; rash.
2. rare respiratory disorders, asthma exacerbations, iritis, uveitis, eyelid skin darkening.
3. very rare chest pain, pharyngitis.
4. eye itching, allergic conjunctivitis, cataract, conjunctival edema, secretions, photophobia, superficial punctate keratitis, headache, high blood pressure.
Glaucoma commonly used drugs
1. prostaglandin derivatives such as latanoprost (Xalatan), bimatoprost (trade name Lumigan) and travoprost (Travatan) can increase outflow of aqueous humor uveoscleral . Bimatoprost also increases trabecular outflow.
2. topical β-adrenergic such as timolol, levobunolol (Betagan), and betaxolol can decrease receptor antagonist of aqueous humor production of ciliary body .
3. Alpha2-adrenergic agonists such as brimonidine (Alphagan) with dual working mechanism, can reduce aqueous humor production and increase trabecular outflow.
4. one case of the selective reduction similar to epinephrine and dipivefrin (Propine) increase outflow of aqueous humor through trabecular meshwork and possibly through uveoscleral outflow pathway, probably by a β2-agonist action.
5. miotic agents (parasympathomimetics), if ciliary muscle contraction Roca works, it can tighten the trabecular and allow increaseing outflow of aqueous humor. Ecothiopate is used for chronic glaucoma.
6. dorzolamide (Trusopt), brinzolamide (Azopt), by inhibiting carbonic anhydrase acetazolamide of ciliary body, reduce aqueous humor secretion of carbonic anhydrase inhibitors.
7. Physostigmine is also used to treat glaucoma and delayed gastric emptying.
The above information is edited by the lookchem of Tian Ye.
Bimatoprost - timolol maleate compound eye drops
In July 2006 , bimatoprost-timolol maleate compound eye drops developed by the United States company obtained approval from the European drug regulatory authority for reducing intraocular pressure or ocular hypertension of open-anglepatients glaucoma patients who do not respond adequately to the β-blockers or prostaglandin like treatment .
The compound eye drops containing 0.03% bimatoprost and 0.5% timolol maleate, once a day administration is able to provide clinically effective pressure control, the effect is better than single Bima latanoprost or timolol maleate.
Clinical trials prove that the drug has an excellent tolerability, including the incidence of ocular hyperemia40% lower compared to single bimatoprost .
Originator
Allergan (US)
Check Digit Verification of cas no
The CAS Registry Mumber 155206-00-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,5,2,0 and 6 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 155206-00:
(8*1)+(7*5)+(6*5)+(5*2)+(4*0)+(3*6)+(2*0)+(1*0)=101
101 % 10 = 1
So 155206-00-1 is a valid CAS Registry Number.
InChI:InChI=1/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3+,17-16+/t20-,21+,22+,23-,24+/m0/s1
155206-00-1Relevant articles and documents
A new synthetic approach to prostaglandin analogues: Synthesis of bimatoprost via lipase enzymatic catalysis
Kamidi, Vijendhar,Kale, Pooja,Boodida, Sathyanarayana
, p. 2767 - 2770 (2017)
A simple, convenient and efficient synthetic approach for the synthesis of (15S) bimatoprost (4) via lipase enzyme mediated stereo selective reduction from chiral precursor Corey lactone diol as substrate was described. Swern oxidation, lipase enzymatic reduction and Wittig reaction conditions are used as key steps for the synthesis of bimatoprost. This method was found to be an efficient with considerable yield, cost effective and minimized the synthetic steps compared to reported procedures.
PROCESS FOR THE PREPARATION OF A NITRIC OXIDE DONATING PROSTAGLANDIN ANALOGUE
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, (2019/09/12)
The present invention relates to a process for preparing the hexanoic acid, 6-(nitrooxy)-, (1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]- 3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl ester of formula (I). In accordance with the present invention, the compound (I) can be efficiently prepared with high purity by coupling bimatoprost in a boronate protected form with 6-(nitrooxy)hexanoyl chloride and removing the boronate protecting group. The 6-(nitrooxy)hexanoyl chloride intermediate is prepared by ring-opening reaction of 2-caprolactone and subsequent nitration of the 6-hydroxyhexanoic acid potassium salt with a mixture of HNO3 and H2SO4 in dichloromethane.
PROCESS FOR THE PREPARATION OF BIMATOPROST
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, (2017/11/15)
It is provided a process for the preparation of bimatoprost, which comprises: a) reacting a compound of formula (III) with ethylamine in the presence of a suitable solvent; and b) deprotecting compound obtained in step a) to obtain bimatoprost, wherein R1 is selected from (C1-C16)alkyl, (C1C16)haloalkyl, (C2-C16)alkenyl, (C2-C16)haloalkenyl, (C1-C16)alkoxy(C1-C16)alkyl, aryl, (C1-C16)alkylaryl, allyl, - (CH2-CH2-O)n-CH3 wherein n = 1, 2, 3 or 4, and -CH(O-CH2-CH2)2; R2 is selected from H, (C1-C16)alkyl, (C1-C16)haloalkyl, (C2-C16)alkenyl, (C2- C16)haloalkenyl, (C1-C16)alkoxy(CrC16)alkyl, aryl, (C1-C16)alkylaryl, allyl; or, alternatively, R1 and R2 taken together are selected from -CH2-CH2-CH2-, -CH2-CH2-, -O-CH2-CH2-, and -O-CH=CH-. There are also provided intermediates useful in such preparation process.