Dorzolamide | CAS#120279-96-1 | carbonic anhydrase inhibitor

MedKoo Cat#: 317636 | Name: Dorzolamide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dorzolamide is a carbonic anhydrase inhibitor. It is an anti-glaucoma agent, and acts by decreasing the production of aqueous humour. It is administered as a topical ophthalmic in the form of a 2% solution.

Chemical Structure

Dorzolamide

CAS#120279-96-1 (free base)

Theoretical Analysis

MedKoo Cat#: 317636

Name: Dorzolamide

CAS#: 120279-96-1 (free base)

Chemical Formula: C10H16N2O4S3

Exact Mass: 324.0272

Molecular Weight: 324.43

Elemental Analysis: C, 37.02; H, 4.97; N, 8.63; O, 19.73; S, 29.65

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 400.00	2 weeks
50mg	USD 800.00	2 Weeks

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Related CAS #

120279-96-1 (free base) 130693-82-2 (HCl)

Synonym

Dorzolamide; Trusopt; 4S,6S-Dorzolamide; Dorzolamida; L-671,152; L671,152; L 671,152; MK-507; MK507; MK 507;

IUPAC/Chemical Name

(4S,6S)-4-(ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide

InChi Key

IAVUPMFITXYVAF-XPUUQOCRSA-N

InChi Code

InChI=1S/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1

SMILES Code

O=S(C(S1)=CC([C@@H](NCC)C[C@@H]2C)=C1S2(=O)=O)(N)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dorzolamide (L671152) is a potent carbonic anhydrase II inhibitor, with IC50 values of 0.18 nM and 600 nM for red blood cell CA-II and CA-I respectively.

In vitro activity:

Component A, caused by an inward flux of CO(2) and its subsequent hydration by CA-II, was blocked by dorzolamide in a dose-dependent manner with an 50% inhibitory concentration (IC)(50) of 2.4 micro M (95% confidence interval: 0.5 -10.85 microM). Dorzolamide significantly inhibits CA activity in BCECs at micromolar levels. Reference: Invest Ophthalmol Vis Sci. 2002 Oct;43(10):3273-8. https://pubmed.ncbi.nlm.nih.gov/12356834/

In vivo activity:

Mice were treated with dorzolamide (3, 10, or 30 mg/kg/day, i.p.) and/or mitomycin C (1 mg/kg, i.p.) weekly for 3 weeks. Treatment with mitomycin C increased TXNIP level in EAC solid tumors in mice. Likewise, treatment with dorzolamide upregulated TXNIP and p53 while downregulated bcl-2. Reference: . Naunyn Schmiedebergs Arch Pharmacol. 2015 Dec;388(12):1271-82. https://pubmed.ncbi.nlm.nih.gov/26264806/

Preparing Stock Solutions

The following data is based on the product molecular weight 324.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Han X, Yang S, Kam WR, Sullivan DA, Liu Y. The Carbonic Anhydrase Inhibitor Dorzolamide Stimulates the Differentiation of Human Meibomian Gland Epithelial Cells. Curr Eye Res. 2020 Dec;45(12):1604-1610. doi: 10.1080/02713683.2020.1772832. Epub 2020 May 31. PMID: 32434386. 2. Srinivas SP, Ong A, Zhai CB, Bonanno JA. Inhibition of carbonic anhydrase activity in cultured bovine corneal endothelial cells by dorzolamide. Invest Ophthalmol Vis Sci. 2002 Oct;43(10):3273-8. PMID: 12356834. 3. Abutaleb NS, Elhassanny AEM, Flaherty DP, Seleem MN. In vitro and in vivo activities of the carbonic anhydrase inhibitor, dorzolamide, against vancomycin-resistant enterococci. PeerJ. 2021 Mar 30;9:e11059. doi: 10.7717/peerj.11059. PMID: 33850651; PMCID: PMC8018244. 4. Ali BM, Zaitone SA, Shouman SA, Moustafa YM. Dorzolamide synergizes the antitumor activity of mitomycin C against Ehrlich's carcinoma grown in mice: role of thioredoxin-interacting protein. Naunyn Schmiedebergs Arch Pharmacol. 2015 Dec;388(12):1271-82. doi: 10.1007/s00210-015-1163-9. Epub 2015 Aug 12. PMID: 26264806.

In vitro protocol:

In vivo protocol:

1. Abutaleb NS, Elhassanny AEM, Flaherty DP, Seleem MN. In vitro and in vivo activities of the carbonic anhydrase inhibitor, dorzolamide, against vancomycin-resistant enterococci. PeerJ. 2021 Mar 30;9:e11059. doi: 10.7717/peerj.11059. PMID: 33850651; PMCID: PMC8018244. 2. Ali BM, Zaitone SA, Shouman SA, Moustafa YM. Dorzolamide synergizes the antitumor activity of mitomycin C against Ehrlich's carcinoma grown in mice: role of thioredoxin-interacting protein. Naunyn Schmiedebergs Arch Pharmacol. 2015 Dec;388(12):1271-82. doi: 10.1007/s00210-015-1163-9. Epub 2015 Aug 12. PMID: 26264806.

1: Konstas AG, Schmetterer L, Katsanos A, Hutnik CML, Holló G, Quaranta L, Teus MA, Uusitalo H, Pfeiffer N, Katz LJ. Dorzolamide/Timolol Fixed Combination: Learning from the Past and Looking Toward the Future. Adv Ther. 2021 Jan;38(1):24-51. doi: 10.1007/s12325-020-01525-5. Epub 2020 Oct 27. PMID: 33108623; PMCID: PMC7854404. 2: Ponticello GS, Sugrue MF, Plazonnet B, Durand-Cavagna G. Dorzolamide, a 40-year wait. From an oral to a topical carbonic anhydrase inhibitor for the treatment of glaucoma. Pharm Biotechnol. 1998;11:555-74. PMID: 9760696. 3: Ormrod D, McClellan K. Topical dorzolamide 2%/timolol 0.5%: a review of its use in the treatment of open-angle glaucoma. Drugs Aging. 2000 Dec;17(6):477-96. doi: 10.2165/00002512-200017060-00005. PMID: 11200308. 4: Balfour JA, Wilde MI. Dorzolamide. A review of its pharmacology and therapeutic potential in the management of glaucoma and ocular hypertension. Drugs Aging. 1997 May;10(5):384-403. doi: 10.2165/00002512-199710050-00006. PMID: 9143858. 5: Martens-Lobenhoffer J, Banditt P. Clinical pharmacokinetics of dorzolamide. Clin Pharmacokinet. 2002;41(3):197-205. doi: 10.2165/00003088-200241030-00004. PMID: 11929320. 6: Pfeiffer N. Dorzolamide: development and clinical application of a topical carbonic anhydrase inhibitor. Surv Ophthalmol. 1997 Sep-Oct;42(2):137-51. doi: 10.1016/s0039-6257(97)00053-2. PMID: 9381367. 7: Martin XD, Danese M. Dorzolamide-induced immune thrombocytopenia: a case report and literature review. J Glaucoma. 2001 Apr;10(2):133-5. doi: 10.1097/00061198-200104000-00011. PMID: 11316096. 8: Loftsson T, Jansook P, Stefánsson E. Topical drug delivery to the eye: dorzolamide. Acta Ophthalmol. 2012 Nov;90(7):603-8. doi: 10.1111/j.1755-3768.2011.02299.x. Epub 2012 Jan 23. PMID: 22269010. 9: Bron AM, Emmerich KH. Latanoprost versus combined timolol and dorzolamide. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S148-54. doi: 10.1016/s0039-6257(02)00290-4. PMID: 12204712. 10: Sugrue MF. The preclinical pharmacology of dorzolamide hydrochloride, a topical carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1996 Fall;12(3):363-76. doi: 10.1089/jop.1996.12.363. PMID: 8875343. 11: Katz LJ, Simmons ST, Craven ER. Efficacy and safety of brimonidine and dorzolamide for intraocular pressure lowering in glaucoma and ocular hypertension. Curr Med Res Opin. 2007 Dec;23(12):2971-83. doi: 10.1185/030079907X242476. PMID: 17949534. 12: Mitsuyama S, Abe F, Higuchi T. Allergic contact dermatitis due to dorzolamide eyedrops. Contact Dermatitis. 2021 Jan;84(1):58-59. doi: 10.1111/cod.13671. Epub 2020 Aug 24. PMID: 32700819. 13: Carlsen J, Durcan J, Zabriskie N, Swartz M, Crandall A. Nephrolithiasis with dorzolamide. Arch Ophthalmol. 1999 Aug;117(8):1087-8. doi: 10.1001/archopht.117.8.1087. PMID: 10448757. 14: Thangavel R, Surve A, Azad S, Kumar V. Dramatic response to topical dorzolamide in X-linked retinoschisis. Indian J Ophthalmol. 2020 Jul;68(7):1466-1467. doi: 10.4103/ijo.IJO_2061_19. PMID: 32587200; PMCID: PMC7574065. 15: Nivean PD, Ariga M, Chithra MR, Gohil P, Das S, Jaideep G. Efficacy of dorzolamide in improving ocular blood flow in patients with open-angle glaucoma: The Indian carbonic anhydrase inhibitor trial. Indian J Ophthalmol. 2022 Dec;70(12):4164-4167. doi: 10.4103/ijo.IJO_1055_22. PMID: 36453306; PMCID: PMC9940594. 16: Dong Y, Sawada Y, Cui J, Hayakawa M, Ogino D, Ishikawa M, Yoshitomi T. Dorzolamide-induced relaxation of isolated rabbit ciliary arteries mediated by inhibition of extracellular calcium influx. Jpn J Ophthalmol. 2016 Mar;60(2):103-10. doi: 10.1007/s10384-015-0423-z. Epub 2016 Jan 12. PMID: 26759121. 17: Martinez A, Gonzalez F, Capeans C, Perez R, Sanchez-Salorio M. Dorzolamide effect on ocular blood flow. Invest Ophthalmol Vis Sci. 1999 May;40(6):1270-5. PMID: 10235564. 18: Kouchak M, Bahmandar R, Bavarsad N, Farrahi F. Ocular Dorzolamide Nanoliposomes for Prolonged IOP Reduction: in-vitroand in-vivo Evaluation in Rabbits. Iran J Pharm Res. 2016 Winter;15(1):205-12. PMID: 27610160; PMCID: PMC4986113. 19: Kobayashi M, Naito K. [Pharmacological profiles of the potent carbonic anhydrase inhibitor dorzolamide hydrochloride, a topical antiglaucoma agent]. Nihon Yakurigaku Zasshi. 2000 Jun;115(6):323-8. Japanese. doi: 10.1254/fpj.115.323. PMID: 10948564. 20: Shimokawa S, Fujiwara K, Murakami Y, Funatsu J, Nakatake S, Yoshida N, Sonoda KH, Ikeda Y. Effect of Topical Dorzolamide on Cystoid Macular Edema in Retinitis Pigmentosa. Ophthalmol Retina. 2020 Oct;4(10):1036-1039. doi: 10.1016/j.oret.2020.05.012. Epub 2020 May 24. PMID: 32454228.