Details of the Drug

General Information of Drug (ID: DMVGPMX)

Drug Name
Fosfomycin
Synonyms
FCM; Phosphomycin; Phosphonemycin; Phosphonomycin; Priomicina; Veramina; Disodium fosfomycin; Disodium phosphonomycin; Fosfocina disodium salt; Fosfomycin disodium; Fosfomycin disodium salt; Fosfomycin sodium; Fosfomycin sodium salt; Fosmicin S; Phosphomycin disodium salt; Phosphonomycin disodium salt; Phosphonomycin sodium; Sodium fosfomycin; MK 955; FOM-Na; Fosfomycin sodium (JP15); Fosmicin S (TN); Fosfomycin (USAN/INN); L-cis-1,2-epoxypropylphosphonic acid; Disodium (1R,2S)-(1,2-epoxypropyl)phosphonate; Disodium[(2r,3s)-3-methyloxiran-2-yl]phosphonate; [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid; Phosphonic acid, (3-methyloxiranyl)-, disodium salt, (2R-cis)-(9CI); (-)-(1R,2S)-(1,2-Epoxypropyl)phosphonicacid; (1R,2S)(-)-(1,2-Epoxypropyl)phosphonic acid disodium salt; (1R,2S)-(1,2-Epoxypropyl)phosphonic acid; (1R,2S)-epoxypropylphosphonate; (1R,2S)-epoxypropylphosphonic acid; (2R-cis)-(3-Methyloxiranyl)phosphonic acid disodium salt
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Urinary tract infection GC08 Approved [2]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01XX01: Fosfomycin
J01XX: Other antibacterials
J01X: OTHER ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
J01XX01: Fosfomycin
J01XX: Other antibacterials
J01X: OTHER ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
S02AA17: Fosfomycin
S02AA: Antiinfectives
S02A: ANTIINFECTIVES
S02: OTOLOGICALS
S: SENSORY ORGANS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 138.06
Logarithm of the Partition Coefficient (xlogp) -1.4
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1.5 h [3]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
Bioavailability
The bioavailability of drug is 55% [3]
Clearance
The clearance of drug is 17 +/- 4.7 L/h [5]
Elimination
82% of drug is excreted from urine in the unchanged form [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 5.7 (?2.8) hours [6]
Metabolism
The drug is not metabolised [7]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 192.901 micromolar/kg/day [8]
Unbound Fraction
The unbound fraction of drug in plasma is 1% [9]
Vd
The volume of distribution (Vd) of drug is 0.3 L/kg [7]
Water Solubility
The ability of drug to dissolve in water is measured as 50 mg/mL [4]
Chemical Identifiers
Formula
C3H7O4P
IUPAC Name
[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
Canonical SMILES
C[C@H]1[C@H](O1)P(=O)(O)O
InChI
InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
InChIKey
YMDXZJFXQJVXBF-STHAYSLISA-N
Cross-matching ID
PubChem CID
446987
ChEBI ID
CHEBI:28915
CAS Number
23155-02-4
UNII
2N81MY12TE
DrugBank ID
DB00828
TTD ID
D01GYT
INTEDE ID
DR0749
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial UDP-N-acetylglucosamine carboxyvinyltransferase (Bact murA) TTICX3S MURA_ECOLI Inhibitor [10]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Glutathione S-transferase alpha-1 (GSTA1)
Main DME 		DE4ZHS1 GSTA1_HUMAN Substrate [11]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-reactive protein (CRP) OT0RFT8F CRP_HUMAN Gene/Protein Processing [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Experimental Cancer Drug Sensitivity Information

Cancer Drug Sensitivity Data Curated from 2 Cell Line(s) in Central Nervous System Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
GaMG CTRP1 6.8203 8.4428 4.5138 0.9288
SF295 CTRP1 6.8281 8.4128 4.5286 0.8503
Cancer Drug Sensitivity Data Curated from 8 Cell Line(s) in Endometrium Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
HEC-265 CTRP1 6.4071 7.7251 4.6122 0.8604
HEC-6 CTRP1 6.6825 8.1898 4.5519 0.8785
HEC-59 CTRP1 6.7239 8.4601 4.4645 1.2951
HEC-108 CTRP1 6.9323 8.1824 4.654 0.2965
HEC-251 CTRP1 7.2387 8.6359 4.6079 0.2901
KLE CTRP1 7.5808 10.0471 4.223 1.6082
MFE-319 CTRP1 7.7907 14.2373 2.4974 12.4331
Ishikawa (Heraklio) 02 ER- CTRP1 6.2786 7.6367 4.5889 1.1489
⏷ Show the Full List of 8 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 6 Cell Line(s) in Haematopoietic And Lymphoid Tissue Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
BL-70 CTRP1 6.6126 7.7091 4.702 0.3101
MC116 CTRP1 6.6817 7.6585 4.745 0.1629
KE-97 CTRP1 6.6835 8.3518 4.4892 1.2065
HT CTRP1 6.8916 8.2837 4.6024 0.4882
P3HR-1 CTRP1 7.1972 8.6704 4.5805 0.3867
Ku812 CTRP1 7.7682 9.3285 4.5589 0.2211
⏷ Show the Full List of 6 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 1 Cell Line(s) in Kidney Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
VMRC-RCW CTRP1 6.9371 10.9079 3.512 7.6288
Cancer Drug Sensitivity Data Curated from 10 Cell Line(s) in Large Intestine Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
SW48 CTRP1 6.2143 8.2233 4.3043 3.2491
LS513 CTRP1 6.4241 9.3281 3.9263 5.7149
DLD-1 CTRP1 6.4788 7.6734 4.6624 0.5502
LS411N CTRP1 6.674 7.8231 4.6846 0.333
SK-CO-1 CTRP1 6.7724 8.242 4.57 0.7101
COLO205 CTRP1 6.9828 8.1689 4.6771 0.2153
GP2d CTRP1 7.0815 8.7932 4.4904 0.8
C2BBe1 CTRP1 7.1522 9.098 4.4043 1.1368
SNU-C2A CTRP1 7.7909 9.8676 4.3779 0.7294
SW403 CTRP1 7.8743 9.4961 4.5392 0.23
⏷ Show the Full List of 10 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 2 Cell Line(s) in Liver Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
JHH-6 CTRP1 6.3047 7.4402 4.678 0.6344
SNU-449 CTRP1 7.6701 9.7332 4.3794 0.806
Cancer Drug Sensitivity Data Curated from 54 Cell Line(s) in Lung Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
BEN CTRP1 6.1206 7.0241 4.7586 0.4282
DV-90 CTRP1 6.1304 8.0874 4.3169 3.3395
Lu-99 CTRP1 6.2921 8.5654 4.1955 3.9135
NCI-H1930 CTRP1 6.4114 8.465 4.3071 2.819
NCI-H522 CTRP1 6.668 8.8169 4.2909 2.4629
NCI-H650 CTRP1 6.6745 10.5441 3.5174 8.2689
HCC78 CTRP1 6.6961 9.719 3.9104 5.1833
NCI-H1573 CTRP1 6.6966 8.6704 4.3664 1.9205
LCLC-103H CTRP1 6.9167 8.2761 4.6149 0.4282
NCI-H1373 CTRP1 6.925 8.6428 4.4819 0.9817
NCI-H1975 CTRP1 6.9386 8.6408 4.4884 0.9368
VMRC-LCD CTRP1 6.955 9.9556 3.9518 4.3155
NCI-H1915 CTRP1 6.9635 8.6605 4.4914 0.8991
NCI-H810 CTRP1 6.965 8.6006 4.5147 0.7912
NCI-H2029 CTRP1 6.9804 8.3392 4.6165 0.3865
COR-L279 CTRP1 6.9853 8.518 4.5537 0.6104
NCI-H2126 CTRP1 6.9859 8.2091 4.6643 0.2457
NCI-H1793 CTRP1 6.9868 9.4596 4.1816 2.6596
LCLC-97TM1 CTRP1 7.0221 9.4553 4.201 2.477
NCI-H82 CTRP1 7.0336 8.5614 4.5569 0.564
NCI-H661 CTRP1 7.0465 10.1265 3.927 4.3101
RERF-LC-KJ CTRP1 7.1024 8.4135 4.6356 0.2731
HCC33 CTRP1 7.1096 8.8082 4.4963 0.7517
NCI-H1048 CTRP1 7.1397 8.5251 4.6103 0.3262
NCI-H1792 CTRP1 7.1527 8.8812 4.4866 0.7584
NCI-H1437 CTRP1 7.1564 9.2889 4.3318 1.5105
SHP-77 CTRP1 7.2021 8.6679 4.5832 0.3759
COR-L88 CTRP1 7.2237 8.8024 4.5434 0.4925
NCI-H1568 CTRP1 7.2243 9.2912 4.3609 1.2807
NCI-H1435 CTRP1 7.2662 8.8313 4.5492 0.449
Calu-3 CTRP1 7.2801 9.0807 4.4641 0.7535
NCI-H23 CTRP1 7.2816 9.4074 4.3408 1.3227
EBC-1 CTRP1 7.2963 9.7116 4.2274 1.9246
A-549 CTRP1 7.347 9.9538 4.1533 2.2931
NCI-H727 CTRP1 7.3535 9.4509 4.355 1.1791
EPLC-272H CTRP1 7.3545 9.3201 4.4051 0.9455
NCI-H2286 CTRP1 7.3962 8.7746 4.6165 0.2133
LC-1/sq-SF CTRP1 7.4185 8.7708 4.6256 0.1881
NCI-H1944 CTRP1 7.4458 9.6533 4.3168 1.2742
NCI-H2009 CTRP1 7.4535 9.2942 4.4545 0.6672
NCI-H358 CTRP1 7.4698 9.4289 4.4115 0.8248
DMS 273 CTRP1 7.5372 9.1701 4.5306 0.3716
LXF 289 CTRP1 7.5392 9.7417 4.3227 1.1567
Calu-6 CTRP1 7.6147 9.2536 4.5298 0.3408
Lu-65 CTRP1 7.6389 9.3828 4.4935 0.4309
KNS-62 CTRP1 7.6621 9.009 4.6296 0.1245
COLO 668 CTRP1 7.685 9.3215 4.5317 0.3085
ChaGo-K-1 CTRP1 7.724 9.3931 4.521 0.3201
HCC44 CTRP1 7.8718 9.7466 4.4518 0.4428
NCI-H2405 CTRP1 7.9151 9.9659 4.3903 0.6105
NCI-H1299 CTRP1 7.9266 9.8643 4.4307 0.4783
NCI-H1355 CTRP1 8.0817 9.9486 4.4579 0.341
HARA [Human squamous cell lung carcinoma] CTRP1 8.1854 9.8129 4.54 0.1542
NCI-H1666 CTRP1 8.4148 10.281 4.462 0.2311
⏷ Show the Full List of 54 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 3 Cell Line(s) in Oesophagus Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
KYSE-450 CTRP1 6.6476 8.3821 4.4606 1.4144
KYSE-410 CTRP1 8.3829 10.2055 4.4764 0.2135
KYSE-140 CTRP1 8.5428 10.437 4.4538 0.2145
Cancer Drug Sensitivity Data Curated from 6 Cell Line(s) in Ovary Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
OVMANA CTRP1 6.7931 8.2517 4.5748 0.6714
JHOS-4 CTRP1 6.7953 8.8955 4.3217 2.0552
COV318 CTRP1 6.9889 8.0273 4.7273 0.1128
EFO-21 CTRP1 7.1203 10.9149 3.6181 6.4021
HEY A8 CTRP1 7.1244 8.5598 4.5924 0.387
SK-OV-3 CTRP1 7.2209 9.2699 4.3677 1.2498
⏷ Show the Full List of 6 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 10 Cell Line(s) in Pancreas Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
PaTu 8902 CTRP1 6.7047 8.3966 4.4811 1.2261
HPAC CTRP1 6.8317 8.3871 4.5399 0.7943
SUIT-2 CTRP1 6.8328 12.0408 2.9127 12.2905
Capan-2 CTRP1 7.0116 11.8601 3.1153 10.3513
CFPAC-1 CTRP1 7.1666 9.0547 4.4271 1.013
QGP-1 CTRP1 7.1942 9.3331 4.3313 1.4693
Panc 03.27 CTRP1 7.3715 8.9495 4.5469 0.4018
KP-3 CTRP1 7.5277 12.8853 2.9618 10.0849
HuP-T4 CTRP1 7.9235 9.5744 4.5298 0.2345
Panc 10.05 CTRP1 8.0192 10.1992 4.3464 0.6991
⏷ Show the Full List of 10 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 3 Cell Line(s) in Pleura Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
NCI-H2052 CTRP1 6.7357 9.737 3.9253 4.9801
MSTO-211H CTRP1 6.9703 9.9095 3.9803 4.0797
NCI-H28 CTRP1 7.7171 10.2002 4.223 1.4643
Cancer Drug Sensitivity Data Curated from 1 Cell Line(s) in Prostate Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
PaCa-3 CTRP1 7.0254 9.4698 4.1966 2.5001
Cancer Drug Sensitivity Data Curated from 5 Cell Line(s) in Skin Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
Hs 852.T CTRP1 6.2751 8.484 4.2223 3.7442
Hs 936.T CTRP1 6.4581 11.0507 3.1337 11.8121
Hs 944.T CTRP1 6.8468 9.0058 4.3012 2.1065
G-361 CTRP1 7.3844 9.0165 4.528 0.4537
COLO 741 CTRP1 7.5526 9.0842 4.5661 0.2744
Cancer Drug Sensitivity Data Curated from 1 Cell Line(s) in Soft Tissue Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
G-401 CTRP1 7.9253 12.3378 3.4394 5.9593
Cancer Drug Sensitivity Data Curated from 6 Cell Line(s) in Stomach Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
MKN7 CTRP1 7.0885 9.229 4.3248 1.6317
SH-10-TC CTRP1 7.1877 8.4172 4.6648 0.1761
NUGC-4 CTRP1 7.2072 8.8546 4.5181 0.5934
Fu97 CTRP1 7.4801 9.2995 4.4629 0.6189
MKN74 CTRP1 7.816 10.1456 4.2854 1.083
SNG-M CTRP1 7.1347 9.4443 4.2598 1.9486
⏷ Show the Full List of 6 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 1 Cell Line(s) in Upper Aerodigestive Tract Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
HSC-2 CTRP1 7.3507 8.7809 4.5982 0.2709
Cancer Drug Sensitivity Data Curated from 5 Cell Line(s) in Urinary Tract Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
HT-1376 CTRP1 6.6127 9.8868 3.7841 6.3588
RT-4 CTRP1 6.8933 10.0864 3.8593 5.1256
KMBC-2 CTRP1 7.1967 9.9262 4.0914 2.9095
UM-UC-3 CTRP1 7.3355 8.9241 4.5424 0.4338
5637 CTRP1 7.8043 9.2718 4.5905 0.1552

References

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2 Fosfomycin FDA Label
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6 FDA Approved Drug Products: Monurol (fosfomycin tromethamine)
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8 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
9 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
10 Evidence that the fosfomycin target Cys115 in UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) is essential for product release. J Biol Chem. 2005 Feb 4;280(5):3757-63.
11 Formation of an adduct between fosfomycin and glutathione: a new mechanism of antibiotic resistance in bacteria. Antimicrob Agents Chemother. 1988 Oct;32(10):1552-6.
12 [Successful treatment of MRSA-associated glomerulonephritis with antibiotic therapy]. Nihon Jinzo Gakkai Shi. 2003;45(1):37-41.