BIMATOPROST

Search structure
Trade Names:
Synonyms:
Status: Approved (2001)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: S01EE03
UNII: QXS94885MZ

Structure
InChI Key AQOKCDNYWBIDND-FTOWTWDKSA-N
Smile CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCc1ccccc1
InChI
InChI=1S/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

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H37NO4
Molecular Weight 415.57
AlogP 3.15
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 12.0
Polar Surface Area 89.79
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 30.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Prostanoid FP receptor agonist KEGG PubMed PubMed PubMed PubMed
Primary Target
FP receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 40400 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypotrichosis 4 D007039 ClinicalTrials
Glaucoma 4 D005901 ClinicalTrials
Graves Ophthalmopathy 3 D049970 ClinicalTrials
Alopecia 2 D000505 ClinicalTrials
Alopecia 2 D000505 ClinicalTrials
Vitiligo 0 D014820 ClinicalTrials

Side Effects from Label

Side effects Relative Frequency (%) Labels
Eye disorders Conjunctival hyperaemia 56.1
Eye disorders Growth of eyelashes 53.6
Eye disorders Conjunctival hyperaemia 44.7
Eye disorders Growth of eyelashes 42.6
Eye disorders Eye pruritus 17.6
Eye disorders Eye pruritus 14.6
Eye disorders Conjunctival hyperaemia 13.3
Eye disorders Dry eye 11.6
Eye disorders Blepharal pigmentation 11.4
Eye disorders Eye irritation 10.4
General disorders and administration site conditions Sensation of foreign body 9.9
Eye disorders Eye pain 9.3
Eye disorders Dry eye 8.0
Eye disorders Visual impairment 7.7
Eye disorders Eye irritation 7.0
Eye disorders Photophobia 6.8
Eye disorders Eye irritation 6.6
Eye disorders Blepharal pigmentation 5.5
General disorders and administration site conditions Sensation of foreign body 5.5
Eye disorders Eyelash discolouration 5.2
Eye disorders Eye pain 5.1
Eye disorders Visual impairment 5.1
Eye disorders Growth of eyelashes 5.0
Eye disorders Visual impairment 4.6
Eye disorders Eye discharge 4.1
Eye disorders Eyelids pruritus 4.1
Eye disorders Erythema of eyelid 3.8
Eye disorders Eye irritation 3.5
Eye disorders Conjunctival hyperaemia 3.4
Eye disorders Eye pain 3.3
Eye disorders Eye pruritus 3.3
Eye disorders Eyelash discolouration 3.2
Eye disorders Asthenopia 3.1
Eye disorders Erythema of eyelid 3.0
Eye disorders Blepharitis 2.9
Eye disorders Cataract 2.9
Eye disorders Eye discharge 2.7
Eye disorders Eye irritation 2.7
Eye disorders Lacrimation increased 2.7
Eye disorders Blepharitis 2.5
Eye disorders Keratitis 2.5
Eye disorders Lacrimation increased 2.5
Eye disorders Keratitis 2.3
Eye disorders Dry eye 2.1
General disorders and administration site conditions Pain 2.1
General disorders and administration site conditions Sensation of foreign body 2.1
Eye disorders Conjunctival oedema 1.9
Vascular disorders Hypertension 1.9
Infections and infestations Rhinitis 1.9
Eye disorders Blepharitis 1.7
Vascular disorders Hypertension 1.7
General disorders and administration site conditions Pain 1.7
Eye disorders Photophobia 1.7
Eye disorders Conjunctivitis allergic 1.5
Eye disorders Lacrimation increased 1.5
General disorders and administration site conditions Asthenia 1.4
Eye disorders Conjunctivitis allergic 1.4
Endocrine disorders Hirsutism 1.4
General disorders and administration site conditions Asthenia 1.3
Eye disorders Asthenopia 1.3
Eye disorders Cataract 1.3
Eye disorders Conjunctival oedema 1.3
Infections and infestations Infection 1.3
Eye disorders Cataract 1.2
Eye disorders Conjunctival oedema 1.2
Eye disorders Corneal erosion 1.2
Cardiac disorders Dizziness 1.2
Eye disorders Eye irritation 1.2
Endocrine disorders Hirsutism 1.1
Eye disorders Corneal erosion 1.0
Psychiatric disorders Depression 1.0
General disorders and administration site conditions Asthenia 0.8
Eye disorders Corneal erosion 0.8
Cardiac disorders Dizziness 0.8
Eye disorders Erythema of eyelid 0.8
Eye disorders Eye discharge 0.8
Vascular disorders Hypertension 0.8
General disorders and administration site conditions Pain 0.8
Infections and infestations Infection 0.6
Cardiac disorders Dizziness 0.5
Eye disorders Asthenopia 0.4
Eye disorders Blepharal pigmentation 0.4
Psychiatric disorders Depression 0.4
Eye disorders Eyelash discolouration 0.4
Eye disorders Eyelids pruritus 0.4
Infections and infestations Infection 0.4
Eye disorders Photophobia 0.4
Infections and infestations Rhinitis 0.4
Eye disorders Eyelids pruritus 0.2

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Eye disorders
38.88
Skin and subcutaneous tissue disorders
19.34
General disorders and administration site conditions
11.84
Injury, poisoning and procedural complications
8.68
Nervous system disorders
5.48
Immune system disorders
2.8

Cross References

Resources Reference
CAS NUMBER 155206-00-1
ChEBI 51230
ChEMBL CHEMBL1200963
DrugBank DB00905
DrugCentral 371
EPA CompTox DTXSID30895042
FDA SRS QXS94885MZ
Human Metabolome Database HMDB0015041
Guide to Pharmacology 1958
PDB 15M
PharmGKB PA164748867
PubChem 5311027
SureChEMBL SCHEMBL24425
ZINC ZINC000004474405
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