betalactam ii dai hoc 2012.sv
TRANSCRIPT
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CEPHALOSPORIN
N
NH
O
O
R1H H
1
3
4
5
67
Cephalosporin
S
2
COOH
R2
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12
3
45678
N
S
H HN
COOH
O
H
C
OAcO
CH2CH2CH2CH
H2N
COOH
nhanh ben 7-aminoadipic
Cephalosporin C
7-aminocephalosporinic acid (7-AC
1945: Cephalosporium acremonium
Peni N, cephalosporin P1, cephalosporin C
Cepha C :
- hoat tnh KK khiem ton, nhng hoat tnh tren S. aureus.- ben vi penicillinase cua Bacillus subtills
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Cephalosporin C (thin nhin)
CEPHALOSPORIN BN TNG HP
- M rong pho KK sang gram am- Gia tang kha nang khang lai beta lactamase- Cai thien ve dc ong hoc
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azetidine-2-on
NH +
OHN
S
dihydrothiazine
NO
S
cephem
Cephalosporin = Azetidin-2-on + dihydrothiazin(cephem)
N
NH
O
O
R1H H
1
3
4
5
67
S
COOH
R2
Cephalosporin
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N
NH
O
O
R1OCH3
H
1
3
4
5
67
S
COOH
R2
Cephamycin
N
NH
O
O
R1H H
1
3
4567
H2C
COOH
R2
Carbacephem
N
NH
O
O
R1R3
H
1
3
4
5
67
O
COOH
R2
Oxacephem
DAN CHAT CEPHEM
Khung cephalosporin ni chung bn hn penicillin i vi acid v -lactamase
Loracarbefcefoxitin
latamoxefO
NH
O
NH2
H H
COOHCl
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Cephalosprin INHOM 1: cefalotin,NHOM 2: cefaloridin, cefazolin,NHOM 3: cefalexin, cefadroxil, cefaclor,
Cephalosprin the he IICefamandol, cefuroxim, cefoxitin
Cephalosporin the he th IIICefotaxim, ceftriaxon, cefixim, cefepim, moxalactam
Cephalosporin the he th IVCefpirom, cefipim
Cephalosporin the he th V
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N
O
XHNR7
O
R
COOH
R31
37
H
DAN CHAT CEPHEMLien quan cau truc tac dung
12
3
45678
N
SH H
N
COOH
O
H
C
OAcO
CH2CH2CH2CHH
2N
COOH
nhanh ben 7-aminoadipic
Cephalosporin C
7-aminocephalosporinic acid (7-AC
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Ban tong hp t cephalosporin C
IEU CHE
12
3
45678
N
SH H
N
COOH
O
H
C
OAcO
CH2CH2CH2CH
H2N
COOH
nhanh ben 7-aminoadipic
Cephalosporin C
7-aminocephalosporinic acid (7-AC
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IEU CHES
O
HNR1
O
H H
OAc
CO2SiMe3
protecting group
34
7
PCl5R1
Cl
imino chloride
ROHR1
OR
imino ether
H2O
- R1CO2H
S
O
H2NH H
OAc
CO2H
34
7
7ACA
R2 Cl
O
Acid chloride
S
O
HN
H H
OAc
CO2H
34
7
O
R2
Range of cephalosporins
Tng hp 7ACA v cc cht tng ng cephalosporin
HNR1
7
..
O
H
PCl4
Cl
NR1
7
O
H
Cl3P
Cl
Cl
..
..: :
R1
ClO
H
Cl3P=O
C ch to imino chloride
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N
S
O
HNC
O
R
CO2Me
26Me
Me
H
H2O2
N
S
CO2Me
Me
Me
O
N
S
CO2Me
CH2
Me
OHH
N
S
CO2Me
CH3
OHH
N
S
CO2Me
CH3
OH
H
:.. - H
N
S
CO2Me
CH3
H
OH
H
H
N
S
CO2Me
H
CH3
Tng hp 3-methyl cephalosporin t mt penicillin
R
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TNH CHAT VAT LY
- Bot tinh the trang hoac co mau nhe, khong mui.
Vai cephalosporin co mui lu huynh (cefalexin, cefradin).
- Co nang suat quay cc nhat nh
- Pho UV: cau truc cephem cho hai hap thu: 220nm va 260nm
- Pho IR: vung ac trng nhat: 1600-1800cm-1
N
NH
O
O
R1H H
1
3
4
5
67
S
COOH
R2
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C=O ( lactam carbonyl) = 1770-1790 cm-1 / KBr
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Cefaloridine
Ph UV:
- Hai hp thu ti a 240 nm (thienyl) v khang 255 nm (cephem)
- Vng b m (do kim hay -lactamase) hp thu 255nm - 260 nmbin mt , xut hin hp thu 230nm (bin mt sau vi gi do phn tb tip tc phn hy).
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M vong azetidin-2-on d/c acid cephalosporic
Tac nhan ai nhan m vong:
NaOH, KOH: tao muoi cua acid cephalosporic
Cac alcol: tao cac este cua acid cephalosporanic.
N
HHN
R
O
O
HS
R3COOH
N
HHN
R
O
O
HS
R3
COOHH
N
HHN
R
O HS
R3
COOH
-O
A N
Nu- Nu
H+
Nu
HOA TNHTnh khong ben cua vong beta lactam
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cac amin tao amid
N
HHN
R
O
O
HS
R3
COOH
NH2OHN
HHN
R
O
O
HS
R3
COOHNHOH
H
acid hydroxamic
Cephalosporin ben hn trong moi trng acid (so vipenicillin).
HOA TNHTnh khong ben cua vong beta lactam
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Nhom COOH C2, cac cephalosporin the hien nhcac acid , bat bao hoa kha manh:
Tao muoi: muoi Na, dang thuoc tiem
Tao cac este c xem la tien chat (cefuroximacetyl va cefpodoxim procetyl).
N
O
XHN
R7
O
R
COOH
R31
37
H
HOA TNHTnh acid
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Cefuroxime
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Nhom ben: CH3, NH2-COOCH2-(carbamoyloxymethyl), Cl
Nhom d phan ng: CH3-COCH2- (acetoxymethyl)
HOA TNHPhan ng nhom the R3 N
O
XHN
R7
O
R
COOH
R31
37
H
N
S
O
ROCHN
H H
O
OCO2H
esteraseN
S
O
ROCHNH H
OH
CO2H
lacton hoa
N
S
O
ROCHN
H H
OO
Giam hoat tnh khong hoat tnh
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12
3
45678
N
S
H H
N
COOH
O
H
C
OAcO
CH2CH2CH2CH
H2N
COOH
nhanh ben 7-aminoadipic
Cephalosporin C
7-aminocephalosporinic acid (7-AC
S
O CH3
OCO2HO
ROCHN H H
OH
S
CH2
CO2H
ROCHN H H
OHO
+CH3HO
O
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Nhom acylamino 7- tnh ben cephalosporin.
S can tr khong gian gan vong -lactam ngan can tac dungcua -lactamase do vay co t/d bao ve.
ac biet ung trong trng hp cac dan chat -alcoxyimin.
N
O
XHN
R7
O
R
COOH
R31
37
H
HOA TNHNhm acylamino
Cefuroxime natri
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KIEM NGHIEM
(tng t nhom Penicillin)- nh tnh
Pho UV, IR
Sac ky lp mong
Phan ng vi H2SO4, vi formaldehyd/H2SO4
- Kim TK
Ph UV ( hp thu)
Nng sut quay cc
pH
-
- nh lng
Phng phap HPLC
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Cephalosprin INHOM 1: cefalotin, cefapirin, cefacetril
B thuy giai bi cephalosporinase, dung tiemCefalothin, BTH au tien s dung vao 1963.
N
SHN
H H
COOH
O
R
O
R-------------------------------------------------------
Cephalotin
NCH2OAc
S
S Cephapirin
N Cephacetril
7-aminocephalosporinic acid (7-AC
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Nhom nay c s dung bang ng tiem.
Cephalosprin INHOM 2: cefaloridin, cefazolin
N
SHN
H H
COOH
O
R
O
R-----------------------------------------------------------------------------
R3
S
R3
N Cephaloridin
N
NN
NN N
SSCephazolin
CH3
12
3
45678
N
SH H
N
COOH
O
H
C
OAcO
CH2CH2CH2CH
H2N
COOH
nhanh ben 7-aminoadipic
Cephalosporin C
p p (
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Cephalosprin INhm3: cefalexin, cefadroxil, cefradin
Cau truc - amino phan t themmot C*, cau dang R co hoat tnh.
Dung ng uong
N
S
COOH
CH3O
R
cefalexin
HO cefadroxil
cefradin
N
H
O
R
NH2
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cau khuan gram (+), gram (-) va vai trc khuan gram (-).
Tu cau khuan noi chung nhay cam (mot so tu cau e khangvi peni G va ampi nhay cam vi cefazolin).
Cong hieu tren E.coli, Klebsiella pneumoniae, Salmonella
Khong co hoat tnh tren trc khuan gram am san xuatcephalosporinase: Enterobacter, Serratia, Providencia,Pseudomonas.
PHO KHANG KHUANCephalosprin I
C h l i th h II
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Nhng phan t co cau truc thay oi,Co ac tnh khang lai beta lactamase.
- Hypothrombinemie
-
Antabuse
S este hoa khac phuc tnh khong ben cuacefamandol khi c bao quan dang kho
Cefamandol nafat (hat tnh tt trn enterobacter v H. influenzae)
Cephalosprin the he IIcefamandol, cefuroxim, cefoxitin, cefotetan, cefaclor, loracarbef
C h l i th h II
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Cefuroxime natri
Cefuroxime acetyl
Cephalosprin the he IIcefamandol, cefuroxim, cefoxitin, cefotetan, cefaclor, loracarbef
(hat tnh tt trn H.influenzae)
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N
Ar
OR
O
(7-ACA/ADCA)
Syn
( Stabilizing againstmany beta-lactamse )
N
Ar
O
(7-ACA/ADCA)
RO
Anti
( Not stabilizing againstmany beta-lactamse )
C h l i th h II
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Cephalosprin the he IIcefamandol, cefuroxim, cefoxitin, cefotetan, cefaclor, loracarbef
Sodium (6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-
oxo-7-[[(thiophen-2-yl)acetyl]amino]-5-thia-1-
azabicyclo[4.2.0]oct-2-ene-2-carboxylate.
(Cefoxitin natri)
Cephalosprin the he II
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(7S)-7-[(4-Carbamoylcarboxymethylene-1,3-dithietan-2-
yl)carboxamido]-7-methoxy-3-[(1-methyl-1H-tetrazol-5-
yl)thiomethyl]-3-cephem-4-carboxylic acid
(Cefotetan)
Ph khng khun tng t cefoxitin
Cephalosprin the he IIcefamandol, cefuroxim, cefoxitin, cefotetan, cefaclor, loracarbef
Cephalosprin the he II
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Cefaclor
Escherichia coli,
Klebsiella pneumoniae,Neisseria gonorrhoeae
Proteus mirabilis
* Haemophilus influenzae.
loracarbef
Cephalosprin the he IIcefamandol, cefuroxim, cefoxitin, cefotetan, cefaclor, loracarbef
O
NH
O
NH2
H H
COOH
Cl
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Tren cau khuan gram (+) khong bang cephalosporin I.
Tren cau khuan gram (-) cephalosporin II manh hncephalosporin I, ac biet tren cau khuan khang
penicillin. hoat tnh tot oi vi vi khuan gram am (ng ruot e
khang vi cephalosporin I) mac phai tai benh vien:
cefamandol hoat tnh hn tren Enterobacter cefuroxim , cefamandol, cefaclor ac biet co
hoat tnh tren Hemophilus influenzae.
Cephalosprin the he II
Pho khang khuan
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Cephalosporin the he th III
Xuat hien t 1980, nhieu tien bo so vi cac the he trc:
Manh hn oi vi vi khuan gram am, MIC thap.
Phan phoi tot nhng vung cephalosporin I va II
khong en c. Nhom nay gom nhng khang sinh s dung chu yeu
bang ng tiem nhng cung co vai phan t hoat tnhkhi dung uong.
Cephalosporin the he th III
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Cephalosporin the he th III-Sulfocephalosporin
(rat ben oi vi - lactamase)
SO
O
O
N
O CO2H
R3
cefsulodin
Sodium 3-(4-carbamoylpyridiniomethyl)-7-
[(2R)-2-phenyl-2-sulphoacetamido]-3-
cephem-4-carboxylate
S
H
N
O
SO3H
OC
N
C O
NH2
OO
cefsulodin
Cephalosporin the he th III
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Cephalosporin the he th IIIUreido cephalosporin
cefoperazon
(7R)-7-[(R)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarboxamido)-2-(4-
hydroxyphenyl)acetamido]-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-
cephem-4-carboxylic acide
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Cefotiam hexetil
Cephalosporin the he th III
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Methoxyimino cephalosporin: hoat tnh khang khuan manh; gom:cefotaxim, cefmenoxim, ceftriaxon, ceftizoxim, ceftazidim, cefixim,cefpodoxim proxetil, va cefetamet pivoxyl.
Cephalosporin the he th III
N
SHNN
SH2N
N
O
OCH3
O
H
COOH
R3
H
Methoxyimino-cephalosporin
R3
----------------------------------------------------------
O
CH3
O Cefotaxim
NN
N N
CH3
S Cefmenoxim
N
N
N
O
OH
S
H3C
Ceftriaxon
H Ceftizoxim
CH3 Cefetamet
Cephalosporin the he th III
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Ceftazidim
Cephalosporin the he th IIIMethoxyiminocephalosporin
cefpodoxim proxetil
Cephalosporin the he th III
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Cephalosporin the he th IIIMethoxyiminocephalosporin
(6R,7R)-7-[[(Z)-2-(2-aminothiazol-4-yl)-2-[
(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid trihydrate.
(Cefixim)
cefdinir
Cephalosporin the he th III
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Cau truc 1-oxacephem khang manh tren gram (-) hieu kh
Cephalosporin the he th IIIOxacephamycin
(tc dng tng t cefotaxim)
LatamoxefO
CO2NaO
O H
CH3
NN
N
N
OH
HN
O
SF
F
Flomoxef natri
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Hoat tnh manh tren vi khuan gram (-)
Tren chung gram (+) va hieu kh t co thay oi.
Hoat tnh chu yeu tren Enterobacterie a e khang:
cefotaxim, cefmenoxim, ceftriaxon, moxalactam Cefotaxim co MIC rat thap vi Enterobacterie a e
khang, Haemophilus influenzaeva Neisseria(meningitidis va gonorrhoeae).
Cefotaxim tac ong tren nhng vi khuan gram am(tr Pseudomonas aeruginosae) tot hn t 10 en 100lan so vi cac cephalosporin co ien.
Pho khang khuanCephalosporin III
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Cephalosporin the he th IV
Cefpirom (1994)
C3: cyclopentenopyridintang hoat tnh khang caukhuan gram (+) vaenterobacterie, VK tietcephalosporinase.
Cefepim (1994)
C3: 3-(N-methylpyrrolidin).
N
SHN
H H
COOHO
R1-----------------------------------------------------------------------------
R2
O
NOR1
R2
N
SH2N
CH3 N
CH3 NH
3C
Cefpirom
Cefepim
Cephalosporin the he th IV
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Cephalosporin the he th IV
N
S
ON
HN
N
O
H H
O
O
NN
O
CH3
NS
N
H2N
(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)- 2-methoxyiminoacetyl]amino]-3-(imidazo[2,3-f]pyridazin- 4-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0] oct-2-ene-2-carboxylate
Cefozopran
Cephalosporin the he th IV
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Cephalosporin the he th IV
N
S
O
HN
N
O
H H
O
O
O
CH3
S
N
H2N N
1-[[(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)-(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0-oct-2-en-3-yl]methyl]-
5,6,7,8-tetrahydroquinolinium inner salt
Cefquinome
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Cephalosporin the he 1 va 2:
- d phong phau thuat nhat la nhng trng hp conguy c nhiem Staphylococcus sau mo.
- dung trong nhng trng hp nhiem trung ngoaibenh vien
Cephalosporin the he 3 va 4:
- ieu tr nhiem trung Pseudomonas
- ieu tr nhng nhiem trung cha xac nh nhng acbiet nang: nhiem trung nao, ng tieu tren, san phukhoa, ho hap, tieu hoa hoac vung bung, nhiem trungmau mac phai tai benh vien
CH NH CHUNG
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D ng: t hn Penicillin
oc tnh vi than: ac biet oi vi cefaloridin,khi phoi hp vi cac khang sinh khac co oc
tnh than Roi loan ve mau va tac ong antabuse, tranh
dung chung vi ru.
OC TNH
Cac cepha co cha nhom the tetrazolthiomethyl
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M-14659
Cephalosporin the he th V
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Cephalosporin the he th V
-Ceftobiprole inhibits the 2a penicillin-binding protein (PBP 2a) ofMethic i l l in-
resistant Staph yloco ccu s aureusand the PBP 2ofStreptococcus
pneumoniaeas well as the classic PBP2 of MSSA.
- Ceftobiprole is resistant to staphylococcal -lactamase
N
S
O
HN
N
O
H H
O
O
OH
NS
N
H2NN
O
NH
Ceftobiprole
(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-ylidene)- 2-nitroso-1-oxoethyl]amino]-8-oxo-3-[(E)-[2-oxo-1-[(3R)- 3-pyrrolidinyl]-3-pyrrolidinylidene]methyl]-
5-thia-1- azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
http://en.wikipedia.org/wiki/Penicillin-binding_proteinhttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Streptococcus_pneumoniaehttp://en.wikipedia.org/wiki/Streptococcus_pneumoniaehttp://en.wikipedia.org/wiki/Beta-lactamasehttp://en.wikipedia.org/wiki/Beta-lactamasehttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Streptococcus_pneumoniaehttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Beta-lactamasehttp://en.wikipedia.org/wiki/Beta-lactamasehttp://en.wikipedia.org/wiki/Beta-lactamasehttp://en.wikipedia.org/wiki/Streptococcus_pneumoniaehttp://en.wikipedia.org/wiki/Streptococcus_pneumoniaehttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Penicillin-binding_proteinhttp://en.wikipedia.org/wiki/Penicillin-binding_proteinhttp://en.wikipedia.org/wiki/Penicillin-binding_protein -
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Ceftobiprole medocaril. Ceftobiprole medocaril (BAL-5788), a water-soluble cephalosporin
prodrug, belongs to a new class of cephem antibiotics with activity against a wide range of
gram-positive organisms, including MRSA and penicillin-resistant Streptococcus
pneumon iae (PRSP), and g ram-negativepathogenic bacteria .
O
CH3
-
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- Ceftaroline fosamil (10/2010) is a fifth-generation cephalosporin antibiotic. It is
active against methicillin-resistant Staphylococcus aureus (MRSA) and Gram
positive bacteria.
- It retains the activity of later generation cephalosporins having broad
spectrum activity against Gram negative bacteria.
- It is currently being investigated forcommunity-acquired pneumonia and
complicated skin and skin structure infection
N
S
O S
HN
N
O
H H
O
O
O
N
S
N CH3
NS
N
NHPO
HO OH
Ceftaroline f osamil
(6R,7R)-7-[(2Z)-2-ethoxyimino-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[4-(1-methylpyridin-1-ium-4-yl)-1,3-thiazol-2-yl]sulfanyl]
-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
MONOBACTAM
http://en.wikipedia.org/wiki/Cephalosporinhttp://en.wikipedia.org/wiki/Antibiotichttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Gram_positivehttp://en.wikipedia.org/wiki/Gram_positivehttp://en.wikipedia.org/wiki/Gram_negativehttp://en.wikipedia.org/wiki/Community-acquired_pneumoniahttp://en.wikipedia.org/wiki/Complicated_skin_and_skin_structure_infectionhttp://en.wikipedia.org/wiki/Complicated_skin_and_skin_structure_infectionhttp://en.wikipedia.org/wiki/Complicated_skin_and_skin_structure_infectionhttp://en.wikipedia.org/wiki/Complicated_skin_and_skin_structure_infectionhttp://en.wikipedia.org/wiki/Community-acquired_pneumoniahttp://en.wikipedia.org/wiki/Community-acquired_pneumoniahttp://en.wikipedia.org/wiki/Community-acquired_pneumoniahttp://en.wikipedia.org/wiki/Gram_negativehttp://en.wikipedia.org/wiki/Gram_positivehttp://en.wikipedia.org/wiki/Gram_positivehttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Methicillin-resistant_Staphylococcus_aureushttp://en.wikipedia.org/wiki/Antibiotichttp://en.wikipedia.org/wiki/Cephalosporin -
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MONOBACTAM
NO
HNR
O
OH
HOOC
HOOC O
NOH
NH2
_______________________________________________R
Nocardicin A
AZTREONAM
MONOBACTAM
-
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AZTREONAM
Acid (Z)-2[[[(2-amino-4-thiazolyl)[[(2S,3S)-2-methyl-4-oxo-1sulfo-3-azetidinyl]
carbamoyl]methylen]amino]oxy]-2-methyl propionic
HOH
O
H2NH OHCH3
H(S)
(R)(S)N
O
H2N H OHCH3H(R)(S)
OR NO
H2NH
CH3(S)
H
H
(S)
NO
H2NH
CH3(S)
SO3H
H
(S)
NO
NH
CH3(S)
SO3H
HHN
S O
N
H2N
O
COOHH3CH3C
Aztreonam
MONOBACTAM
-
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Pho khang khuan
Aztreonam khong co hoat tnh tren vi khuan gram (+).
Hoat tnh tren vi khuan gram am tng ng vicephalosporin III: Enterobacterie, H. influenzae,Pseudomonas, Neisseria menigitidis
AZTREONAM
Acid (Z)-2[[[(2-amino-4-thiazolyl)[[(2S,3S)-2-methyl-4-oxo-1sulfo-3-azetidinyl]
carbamoyl]methylen]amino]oxy]-2-methyl propionic
COOH
-
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Cai thien tac ong trenEnterobacteriaceae
manh tren gram am ;
ben vi -lactamase;
hp thu tt qua ng ung
(2-carbamoyloxymethyl) 2,2-dimethyl
N
HN
S
N
H2N
N
O
O
O SO3H
Aztreonam
N
HN
S
N
H2N
N
O
O
COOH
O SO3H
OCONH2
Carumonam
N
HN
S
N
H2N
N
O
O
COOH
O SO3H
Tigemonam