Pilocarpine

Details

• Internal ID: 541a7be2-3d23-495d-bd45-32caf86196e7
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
• SMILES (Canonical): CCC1C(COC1=O)CC2=CN=CN2C
• SMILES (Isomeric): CC[C@H]1[C@H](COC1=O)CC2=CN=CN2C
• InChI: InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1
• InChI Key: QCHFTSOMWOSFHM-WPRPVWTQSA-N
• Popularity: 15,397 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₆N₂O₂
• Molecular Weight: 208.26 g/mol
• Exact Mass: 208.121177757 g/mol
• Topological Polar Surface Area (TPSA): 44.10 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.16
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 92-13-7
• Pilokarpin
• Pilocarpol
• Syncarpine
• Pilocarpin
• (+)-Pilocarpine
• Ocusert pilo
• Spersacarpine
• Pilokarpol
• Ocusert pilo-20
• Ocusert Pilo-40
• Ocusert P 20
• ocucarpine
• Isoptocarpine
• Pilocarpine chloride
• Pilocarpinum
• HSDB 3163
• EINECS 202-128-4
• UNII-01MI4Q9DI3
• (3S,4R)-3-Ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)dihydrofuran-2(3H)-one
• (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydrofuran-2(3H)-one
• 01MI4Q9DI3
• CHEBI:8207
• DTXSID1021162
• AI3-50523
• CHEMBL550
• (3S-cis)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone
• Imidazole-5-butyric acid, alpha-ethyl-beta-(hydroxymethyl)-1-methyl-, gamma-lactone
• Pilocarpine [USP:BAN:JAN]
• DTXCID901162
• (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
• (3S,4R)-3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone
• (3S-cis)-3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone
• 2(3H)-Furanone, 3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-, (3S,4R)-
• 92-13-7 (FREE BASE)
• NCGC00023339-09
• 2(3H)-Furanone, 3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-, (3S-cis)-
• Pilocarpine 100 microg/mL in Acetonitrile
• (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one
• beta-Pilocarpine hydrochloride
• 2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (3S,4R)-
• PILOCARPINE (MART.)
• PILOCARPINE [MART.]
• PILOCARPINE (USP-RS)
• PILOCARPINE [USP-RS]
• Pilocarpine (USP:BAN:JAN)
• Pilocarpine nitrate salt
• PILOCARPINE (USP MONOGRAPH)
• PILOCARPINE [USP MONOGRAPH]
• Pilocarpine, (+)-
• CAS-92-13-7
• Pilocarpine (JAN/USP)
• Ocusert pilo-20 (TN)
• Pilocarpina
• 3-Ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydrofuran-2(3H)-one
• Ocucarpine; Ocusert P 20; Ocusert Pilo
• pilocarpine, Cytokine
• Spectrum_001107
• Tocris-0694
• PILOCARPINE [MI]
• Prestwick0_000449
• Prestwick1_000449
• Prestwick2_000449
• Prestwick3_000449
• Spectrum2_001284
• Spectrum3_000546
• Spectrum4_000478
• Spectrum5_001379
• PILOCARPINE [JAN]
• PILOCARPINE [HSDB]
• PILOCARPINE [VANDF]
• PILOCARPINUM [HPUS]
• Lopac0_000950
• Lopac0_000960
• SCHEMBL15146
• BSPBio_000498
• BSPBio_002191
• GTPL305
• KBioGR_000956
• KBioSS_001587
• PILOCARPINE [WHO-DD]
• BIDD:GT0217
• DivK1c_000358
• SPBio_001287
• SPBio_002437
• BPBio1_000548
• CHEBI:39462
• HY-B0726A
• KBio1_000358
• KBio2_001587
• KBio2_004155
• KBio2_006723
• KBio3_001691
• PILOCARPINE [ORANGE BOOK]
• NINDS_000358
• HMS2089K17
• Tox21_110887
• BDBM50008072
• MFCD00153042
• (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]tetrahydrofuran-2-one
• AKOS016010311
• Tox21_110887_1
• (3S-CIS)-3-ETHYLDIHYDRO-4-
• CCG-205031
• DB01085
• SDCCGMLS-0003164.P005
• SDCCGSBI-0050924.P006
• IDI1_000358
• NCGC00023339-03
• NCGC00023339-06
• NCGC00023339-07
• NCGC00023339-08
• NCGC00023339-10
• NCGC00023339-11
• NCGC00023339-12
• NCGC00023339-13
• NCGC00023339-14
• NCGC00023339-16
• NCGC00023339-27
• NCGC00023339-28
• BS-18966
• NCI60_004403
• SBI-0050924.P004
• CS-0013746
• C07474
• D00525
• E87145
• AB00053525-27
• AB00053525_28
• AB00053525_29
• EN300-19632236
• Q411461
• BRD-K85090592-008-05-2
• BRD-K85090592-008-15-1
• SR-01000075339-11
• (3S,4R)-3-Ethyl-4-(1-methyl-1H-imidazol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one
• rel-(3R,4S)-3-ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)dihydrofuran-2(3H)-one
• 102282-25-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.7961	79.61%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Lysosomes	0.8148	81.48%
OATP2B1 inhibitior	-	0.8481	84.81%
OATP1B1 inhibitior	+	0.9471	94.71%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.7000	70.00%
BSEP inhibitior	-	0.8666	86.66%
P-glycoprotein inhibitior	-	0.9781	97.81%
P-glycoprotein substrate	-	0.7484	74.84%
CYP3A4 substrate	-	0.6935	69.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9014	90.14%
CYP3A4 inhibition	+	0.7961	79.61%
CYP2C9 inhibition	-	0.8732	87.32%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9337	93.37%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6931	69.31%
Eye corrosion	-	0.9663	96.63%
Eye irritation	-	0.9534	95.34%
Skin irritation	-	0.7149	71.49%
Skin corrosion	-	0.8888	88.88%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6337	63.37%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.8614	86.14%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6896	68.96%
Acute Oral Toxicity (c)	II	0.7352	73.52%
Estrogen receptor binding	-	0.6961	69.61%
Androgen receptor binding	-	0.6029	60.29%
Thyroid receptor binding	-	0.7986	79.86%
Glucocorticoid receptor binding	-	0.6316	63.16%
Aromatase binding	-	0.5843	58.43%
PPAR gamma	-	0.8130	81.30%
Honey bee toxicity	-	0.9313	93.13%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8254	82.54%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4040	P28482	MAP kinase ERK2	1 nM	Potency	via Super-PRED
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	17.5 nM	EC50	via Super-PRED
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	6.3 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	281.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.76%	97.25%
CHEMBL2581	P07339	Cathepsin D	94.12%	98.95%
CHEMBL1978	P11511	Cytochrome P450 19A1	89.64%	91.76%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.01%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.05%	95.56%
CHEMBL255	P29275	Adenosine A2b receptor	84.93%	98.59%
CHEMBL3401	O75469	Pregnane X receptor	84.31%	94.73%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.98%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.76%	94.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.64%	93.65%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.79%	89.34%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.74%	98.46%

Plants that contains it

• Lolium pratense
• Pilocarpus microphyllus
• Pilocarpus racemosus
• Pilocarpus trachylophus

Cross-Links

• PubChem: 5910
• LOTUS: LTS0172369
• wikiData: Q411461