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MedKoo Cat#: 317627 | Name: Dipivefrin

Description:

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

Dipivefrin is a prodrug of epinephrine, and is used to treat open-angle glaucoma.

Chemical Structure

Dipivefrin
Dipivefrin
CAS#52365-63-6 (free base)

Theoretical Analysis

MedKoo Cat#: 317627

Name: Dipivefrin

CAS#: 52365-63-6 (free base)

Chemical Formula: C19H29NO5

Exact Mass: 351.2046

Molecular Weight: 351.44

Elemental Analysis: C, 64.93; H, 8.32; N, 3.99; O, 22.76

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
52365-63-6 (free base) 64019-93-8 (HCl) 56298-24-9 (R-isomer) 79071-01-5 (R-isomer HCl) 149494-91-7 (S-isomer) 133815-41-5 (S-isomer HCl)
Synonym
Dipivefrin; Dipivefrine; Dipivefrinum; Dipivefrina; (±)-Dipivefrin; DPE
IUPAC/Chemical Name
4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene bis(2,2-dimethylpropanoate)
InChi Key
OCUJLLGVOUDECM-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3
SMILES Code
CC(C)(C)C(OC1=CC=C(C(O)CNC)C=C1OC(C(C)(C)C)=O)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 351.44 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.

Recalculate based on batch purity %
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
1: Groh MJ, Michelson G, Harazny J, Groh M, Koschinsky K. [Changes in retinal blood flow by topical administration of 0.1% dipivefrin]. Ophthalmologe. 1999 Nov;96(11):706-10. German. PubMed PMID: 10631832. 2: Edgar DF, Crabb DP, Rudnicka AR, Lawrenson JG, Guttridge NM, O'Brien CJ. Effects of dipivefrin and pilocarpine on pupil diameter, automated perimetry and LogMAR acuity. Graefes Arch Clin Exp Ophthalmol. 1999 Feb;237(2):117-24. PubMed PMID: 9987628. 3: Rossetti L, Barbieri P, Velati P, Bujtar E, Orzalesi N. The efficacy of the combination of l-moprolol and dipivefrin in reducing the intraocular pressure in primary open-angle glaucoma or in ocular hypertension. Graefes Arch Clin Exp Ophthalmol. 1994 Nov;232(11):670-4. PubMed PMID: 7843592. 4: Michelson G, Groh MJ. Dipivefrin reduces blood flow in the ciliary body in humans. Ophthalmology. 1994 Apr;101(4):659-64. PubMed PMID: 8152760. 5: Albracht DC, LeBlanc RP, Cruz AM, Lamping KA, Siegel LI, Stern KL, Kelley EP, Stoecker JF. A double-masked comparison of betaxolol and dipivefrin for the treatment of increased intraocular pressure. Am J Ophthalmol. 1993 Sep 15;116(3):307-13. PubMed PMID: 8357055. 6: Drake MV, Wilson MR, Harris D, Goodwin L. Levobunolol compared to dipivefrin in African American patients with open angle glaucoma. J Ocul Pharmacol. 1993 Summer;9(2):91-5. Erratum in: J Ocul Pharmacol 1993 Winter;9(4):385. PubMed PMID: 8123096. 7: Wall GM, Kenny JC, Fan TY, Schafer C, Ready MA, Baker JK, Ritter P, Scott BS. Analysis of 3- and 4-monopivaloylepinephrine, degradation products in dipivefrin hydrochloride drug substance and ophthalmic formulations. J Pharm Biomed Anal. 1992 Jun;10(6):465-71. PubMed PMID: 1420470. 8: Satterfield D, Mannis MJ, Glover AT. Unilateral corneal vesicles secondary to dipivefrin therapy. Am J Ophthalmol. 1992 Mar 15;113(3):339-40. PubMed PMID: 1543234. 9: Geyer O, Rothkoff L, Lazar M. Efficacy of adding dipivefrin to a beta-blocker. Ophthalmology. 1990 Oct;97(10):1245-6. PubMed PMID: 2243671. 10: Harper DG, Novack GD, Borrmann LR, Branin MJ. [Dipivefrin: its mechanism of action, clinical efficacy and good tolerance]. Ophtalmologie. 1989 Sep-Dec;3(4):306-7. French. PubMed PMID: 2641142. 11: Parrow KA, Hong YJ, Shin DH, Shi DX, McCarty B. Is it worthwhile to add dipivefrin HCl 0.1% to topical beta 1-, beta 2-blocker therapy? Ophthalmology. 1989 Sep;96(9):1338-41; discussion 1341-2. PubMed PMID: 2571114. 12: Allen RC, Robin AL, Long D, Novack GD, Lue JC, Kaplan G. A combination of levobunolol and dipivefrin for the treatment of glaucoma. Arch Ophthalmol. 1988 Jul;106(7):904-7. PubMed PMID: 3291837. 13: West RH, Gillies WE, Brooks AM. Therapeutic response interactions between timolol maleate and dipivefrin hydrochloride. Aust N Z J Ophthalmol. 1987 May;15(2):131-4. PubMed PMID: 3620185. 14: Ober M, Scharrer A, Dausch D. [Guanethidine/dipivefrin and pilocarpine in the treatment of increased intraocular pressure]. Klin Monbl Augenheilkd. 1987 Feb;190(2):103-4. German. PubMed PMID: 3573660. 15: Tsoy EA, Meekins BB, Shields MB. Comparison of two treatment schedules for combined timolol and dipivefrin therapy. Am J Ophthalmol. 1986 Sep 15;102(3):320-4. PubMed PMID: 3529971. 16: Weinreb RN, Ritch R, Kushner FH. Effect of adding betaxolol to dipivefrin therapy. Am J Ophthalmol. 1986 Feb 15;101(2):196-8. PubMed PMID: 3946535. 17: Ober M, Scharrer A. [Experiences with the effectiveness and tolerance of guanethidine/dipivefrin-AT in the treatment of increased intraocular pressure]. Klin Monbl Augenheilkd. 1986 Jan;188(1):64-6. German. PubMed PMID: 3959479. 18: Dipivefrin: an adrenaline pro-drug for glaucoma. Drug Ther Bull. 1985 Apr 9;23(7):27-8. PubMed PMID: 3987515. 19: Mindel JS, Cohen G, Barker LA, Lewis DE. Enzymatic and nonenzymatic hydrolysis of D,L-dipivefrin. Arch Ophthalmol. 1984 Mar;102(3):457-60. PubMed PMID: 6703997. 20: Mehelas TJ, Kollarits CR, Martin WG. Cystoid macular edema presumably induced by dipivefrin hydrochloride (Propine). Am J Ophthalmol. 1982 Nov;94(5):682. PubMed PMID: 7148952.

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Monocrotaline

Monocrotaline

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