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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:40 UTC
HMDB IDHMDB0014592
Secondary Accession Numbers
  • HMDB14592
Metabolite Identification
Common NameDipivefrin
DescriptionDipivefrin is only found in individuals that have used or taken this drug. It is a prodrug of adrenaline, which is used to treat glaucoma. It is available as ophthalmic solution (eye drops). Dipivefrin is a prodrug with little or no pharmacologically activity until it is hydrolyzed into epinephrine inside the human eye. The liberated epinephrine, an adrenergic agonist, appears to exert its action by stimulating α- and/or β2-adrenergic receptors, leading to a decrease in aqueous production and an enhancement of outflow facility. The dipivefrin prodrug delivery system is a more efficient way of delivering the therapeutic effects of epinephrine, with fewer side effects than are associated with conventional epinephrine therapy.
Structure
Data?1582753196
Synonyms
ValueSource
(+-)-4-[1-Hydroxy-2-(methylamino)ethyl]-O-phenylene divavalateChEBI
1-(3',4'-Dipivaloyloxyphenyl)-2-methylamino-1-ethanolChEBI
4-[1-Hydroxy-2-(methylamino)ethyl]-O-phenylene divavalateChEBI
Dipivalyl epinephrineChEBI
DipivefrinaChEBI
DipivefrineChEBI
DipivefrinumChEBI
(+-)-4-[1-Hydroxy-2-(methylamino)ethyl]-O-phenylene divavalic acidGenerator
4-[1-Hydroxy-2-(methylamino)ethyl]-O-phenylene divavalic acidGenerator
Alcon brand OF dipivefrin hydrochlorideHMDB
DiopineHMDB
GlaucothilHMDB
PMS-DipivefrinHMDB
Pharm-allergan brand OF dipivefrin hydrochlorideHMDB
PropineHMDB
DipivaloylepinephrineHMDB
Dipivefrin perchlorateHMDB
Apo-dipivefrinHMDB
GlaudropsHMDB
Adrenaline dipivalateHMDB
Dipivefrin acetate, (+-)-isomerHMDB
Dipivefrin monophosphate, (+-)-isomerHMDB
Dipivefrin monosulfate, (+-)-isomerHMDB
Dipivefrin tartrate (1:1), (+-)-(R-(r*,r*))-isomerHMDB
Allergan brand OF dipivefrin hydrochlorideHMDB
DipoquinHMDB
Ioquin brand OF dipivefrin hydrochlorideHMDB
Pharmascience brand OF dipivefrin hydrochlorideHMDB
Ratiopharm brand OF dipivefrin hydrochlorideHMDB
D EpifrinHMDB
Dipivefrin citrate (1:1), (+-)-isomerHMDB
Dipivefrin nitrate, (+-)-isomerHMDB
Dipivefrin propanoate, (+-)-isomerHMDB
Dipivefrin tartrate (1:1), (R)-(R-(r*,r*))-isomerHMDB
Apotex brand OF dipivefrin hydrochlorideHMDB
Dipivefrin hydrochlorideHMDB
Dipivefrin hydrochloride, (+-)-isomerHMDB
Dipivefrin, (R)-isomerHMDB
Ratio-dipivefrinHMDB
Chemical FormulaC19H29NO5
Average Molecular Weight351.4373
Monoisotopic Molecular Weight351.204573043
IUPAC Name2-[(2,2-dimethylpropanoyl)oxy]-5-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate
Traditional Namedipivefrin
CAS Registry Number52365-63-6
SMILES
CNCC(O)C1=CC(OC(=O)C(C)(C)C)=C(OC(=O)C(C)(C)C)C=C1
InChI Identifier
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
InChI KeyOCUJLLGVOUDECM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol esters
Sub ClassNot Available
Direct ParentPhenol esters
Alternative Parents
Substituents
  • Phenol ester
  • Phenoxy compound
  • Aralkylamine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Secondary amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.058 g/LNot Available
LogP1.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP3.17ALOGPS
logP3.71ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14ChemAxon
pKa (Strongest Basic)9.33ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.86 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity94.94 m³·mol⁻¹ChemAxon
Polarizability38.65 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.50931661259
DarkChem[M-H]-183.59431661259
DeepCCS[M+H]+191.36430932474
DeepCCS[M-H]-188.7830932474
DeepCCS[M-2H]-223.31630932474
DeepCCS[M+Na]+198.85230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DipivefrinCNCC(O)C1=CC(OC(=O)C(C)(C)C)=C(OC(=O)C(C)(C)C)C=C12357.6Standard polar33892256
DipivefrinCNCC(O)C1=CC(OC(=O)C(C)(C)C)=C(OC(=O)C(C)(C)C)C=C12223.8Standard non polar33892256
DipivefrinCNCC(O)C1=CC(OC(=O)C(C)(C)C)=C(OC(=O)C(C)(C)C)C=C12219.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dipivefrin,1TMS,isomer #1CNCC(O[Si](C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C12150.6Semi standard non polar33892256
Dipivefrin,1TMS,isomer #2CN(CC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C2318.0Semi standard non polar33892256
Dipivefrin,2TMS,isomer #1CN(CC(O[Si](C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C2294.9Semi standard non polar33892256
Dipivefrin,2TMS,isomer #1CN(CC(O[Si](C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C2426.3Standard non polar33892256
Dipivefrin,2TMS,isomer #1CN(CC(O[Si](C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C2573.9Standard polar33892256
Dipivefrin,1TBDMS,isomer #1CNCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C12368.3Semi standard non polar33892256
Dipivefrin,1TBDMS,isomer #2CN(CC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C2573.1Semi standard non polar33892256
Dipivefrin,2TBDMS,isomer #1CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C2784.2Semi standard non polar33892256
Dipivefrin,2TBDMS,isomer #1CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C2808.8Standard non polar33892256
Dipivefrin,2TBDMS,isomer #1CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C2808.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dipivefrin GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9150000000-30a32fb00720193ce9122017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dipivefrin GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-9044000000-b32f8d364631e20e40172017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dipivefrin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 10V, Positive-QTOFsplash10-0f89-0049000000-cef336a5e244ea16b9f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 20V, Positive-QTOFsplash10-0kai-4059000000-c483238390ca6a1eaa682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 40V, Positive-QTOFsplash10-0a59-9351000000-607bb994262a9b1034922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 10V, Negative-QTOFsplash10-0udi-0109000000-2ce96b91437661fde6842016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 20V, Negative-QTOFsplash10-0ue9-2449000000-59429e2be741d17c81172016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 40V, Negative-QTOFsplash10-0udi-3910000000-eb3054746367b77b8eed2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 10V, Positive-QTOFsplash10-0ue9-0019000000-4099393ff81d85a0ef032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 20V, Positive-QTOFsplash10-0f89-0059000000-459602b5970b064ff34c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 40V, Positive-QTOFsplash10-0a4i-9383000000-22ec9c056edfb61e9b132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 10V, Negative-QTOFsplash10-0udi-0019000000-6628a7bbb51fbe187be72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 20V, Negative-QTOFsplash10-0udi-0759000000-ec60a4f35ccc46b4a95a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dipivefrin 40V, Negative-QTOFsplash10-0f79-6692000000-669ea5989d4d3ee824872021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00449 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00449 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00449
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2994
KEGG Compound IDC06963
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDipivefrin
METLIN IDNot Available
PubChem Compound3105
PDB IDNot Available
ChEBI ID4646
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Nakamura M, Shirasawa E, Hikida M: Characterization of esterases involved in the hydrolysis of dipivefrin hydrochloride. Ophthalmic Res. 1993;25(1):46-51. [PubMed:8446367 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Ozakca I, Arioglu E, Guner S, Altan VM, Ozcelikay AT: Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. Pharmacology. 2007;80(4):227-38. Epub 2007 Jul 6. [PubMed:17622774 ]
  3. Prenner L, Sieben A, Zeller K, Weiser D, Haberlein H: Reduction of high-affinity beta2-adrenergic receptor binding by hyperforin and hyperoside on rat C6 glioblastoma cells measured by fluorescence correlation spectroscopy. Biochemistry. 2007 May 1;46(17):5106-13. Epub 2007 Apr 7. [PubMed:17417877 ]
  4. Lucin KM, Sanders VM, Jones TB, Malarkey WB, Popovich PG: Impaired antibody synthesis after spinal cord injury is level dependent and is due to sympathetic nervous system dysregulation. Exp Neurol. 2007 Sep;207(1):75-84. Epub 2007 Jun 2. [PubMed:17597612 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Sanbe A, Tanaka Y, Fujiwara Y, Tsumura H, Yamauchi J, Cotecchia S, Koike K, Tsujimoto G, Tanoue A: Alpha1-adrenoceptors are required for normal male sexual function. Br J Pharmacol. 2007 Oct;152(3):332-40. Epub 2007 Jul 2. [PubMed:17603545 ]
  2. Tomiyama Y, Kobayashi K, Tadachi M, Kobayashi S, Inada Y, Kobayashi M, Yamazaki Y: Expressions and mechanical functions of alpha1-adrenoceptor subtypes in hamster ureter. Eur J Pharmacol. 2007 Nov 14;573(1-3):201-5. Epub 2007 Jul 6. [PubMed:17658513 ]