Dipivefrin hydrochloride is a prodrug of epinephrine, an adrenergic agonist, used as a topical ophthalmic solution to treat open-angle glaucoma. It is synthesized by reacting epinephrine with pivaloyl chloride, forming a dipivaloyl ester that is subsequently converted to the hydrochloride salt. Dipivefrin is slowly hydrolyzed in the eye to release epinephrine, which increases outflow of aqueous humor and reduces intraocular pressure. It is studied for its efficacy and safety in managing glaucoma and for potential applications in other ophthalmic conditions. The compound is important for its role in providing sustained release of epinephrine to the eye, leading to improved efficacy in reducing intraocular pressure.'
dipivefrin hydrochloride : The hydrochloride salt of dipivefrin. It is used topically as eye drops to reduce intra-ocular pressure in the treatment of open-angle glaucoma or ocular hypertension. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 71486 |
| CHEMBL ID | 1200833 |
| CHEBI ID | 4647 |
| SCHEMBL ID | 41350 |
| MeSH ID | M0312742 |
| Synonym |
|---|
| smr001233266 |
| MLS002153922 |
| dipivefrin hcl |
| (+-)-3,4-dihydroxy-alpha-((methylamino)methyl)benzyl alcohol 3,4-dipivalate hydrochloride |
| propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, hydrochloride, (+-)- |
| dipivefrin hydrochloride |
| (1)-4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene dipivalate hydrochloride |
| akpro |
| einecs 264-609-5 |
| dipivefrine hydrochloride |
| dipivalyl epinephrine hydrochloride |
| NCGC00016906-01 |
| cas-64019-93-8 |
| D01017 |
| 64019-93-8 |
| dipivefrin hydrochloride (jan/usp) |
| propine (tn) |
| 2-{3,4-bis[(2,2-dimethylpropanoyl)oxy]phenyl}-2-hydroxy-n-methylethanaminium chloride |
| 1-(3',4'-dipivaloyloxyphenyl)-2-methylamino-1-ethanol hydrochloride |
| 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diyl bis(2,2-dimethylpropanoate) hydrochloride |
| dipivefrine hcl |
| CHEBI:4647 , |
| CHEMBL1200833 |
| HMS1569P06 |
| (rs)-4-(1-hydroxy-2-(methylamino)ethyl)-o-phenylene dipivalate hydrochloride |
| tox21_110675 |
| dtxsid2045494 , |
| dtxcid0025494 |
| dipivefrin hydrochloride [usp:jan] |
| 5qth9uhv0k , |
| unii-5qth9uhv0k |
| dipivefrin hydrochloride [usp monograph] |
| dipivefrin hydrochloride [vandf] |
| dipivefrine hydrochloride [ep monograph] |
| dipivefrine hydrochloride [jan] |
| dipivefrin hydrochloride [orange book] |
| propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, (+/-)-, hydrochloride |
| dipivalylepinephrine hydrochloride |
| (+/-)-3,4-dihydroxy-.alpha.-((methylamino)methyl)benzyl alcohol 3,4-dipivalate hydrochloride |
| dipivefrin hydrochloride [mi] |
| dipivefrine hydrochloride [who-dd] |
| dipivefrin hydrochloride [jan] |
| dipivefrine hydrochloride [mart.] |
| CCG-220632 |
| SCHEMBL41350 |
| VKFAUCPBMAGVRG-UHFFFAOYSA-N |
| dipivefrin (hydrochloride) |
| SR-01000838856-2 |
| sr-01000838856 |
| 2-[(2,2-dimethylpropanoyl)oxy]-4-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate hydrochloride |
| Q27106427 |
| BCP13649 |
| [2-(2,2-dimethylpropanoyloxy)-4-[1-hydroxy-2-(methylamino)ethyl]phenyl] 2,2-dimethylpropanoate;hydrochloride |
| dipivefrine (hydrochloride) |
| 64019-93-8 (hcl) |
| MS-26426 |
| HY-B1323 |
| CS-0013083 |
| AKOS037515482 |
| dipivefrine for system suitability |
| dipivefrin hydrochloride (usp:jan) |
| alcon |
| (+/-)-3,4-dihydroxy-alpha-((methylamino)methyl)benzyl alcohol 3,4-dipivalate hydrochloride |
| propanoic acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene ester, hydrochloride,(+-)- |
| dipivefrin hydrochloride (usp monograph) |
| 4-(1-hydroxy-2-(methylamino)ethyl)benzene-1,2-diyl bis(2,2-dimethylpropanoate) hydrochloride |
| 2-(3,4-bis((2,2-dimethylpropanoyl)oxy)phenyl)-2-hydroxy-n-methylethanaminium chloride |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
| Role | Description |
|---|---|
| adrenergic agonist | An agent that selectively binds to and activates adrenergic receptors. |
| sympathomimetic agent | A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. |
| antiglaucoma drug | Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| hydrochloride | A salt formally resulting from the reaction of hydrochloric acid with an organic base. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Beta-lactamase | Escherichia coli K-12 | Potency | 2.8184 | 0.0447 | 17.8581 | 100.0000 | AID485294 |
| glp-1 receptor, partial | Homo sapiens (human) | Potency | 1.3777 | 0.0184 | 6.8060 | 14.1254 | AID624417; AID743262 |
| TDP1 protein | Homo sapiens (human) | Potency | 9.0349 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| beta-2 adrenergic receptor | Homo sapiens (human) | Potency | 0.7660 | 0.0058 | 6.0263 | 32.6427 | AID492947; AID588463; AID588790 |
| parathyroid hormone/parathyroid hormone-related peptide receptor precursor | Homo sapiens (human) | Potency | 1.9953 | 3.5481 | 19.5427 | 44.6684 | AID743266 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 10.9633 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| DNA polymerase iota isoform a (long) | Homo sapiens (human) | Potency | 89.1251 | 0.0501 | 27.0736 | 89.1251 | AID588590 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| beta-2 adrenergic receptor | Homo sapiens (human) | EC50 (µMol) | 7.1300 | 0.0016 | 1.8759 | 8.4400 | AID588763 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21 | Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
| AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 1 (11.11) | 29.6817 |
| 2010's | 6 (66.67) | 24.3611 |
| 2020's | 2 (22.22) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (23.74) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 9 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||